Mini-Reviews in Medicinal Chemistry

Author(s): Ankit Jain and Poonam Piplani*

DOI: 10.2174/1389557519666190312162601

Exploring the Chemistry and Therapeutic Potential of Triazoles: A Comprehensive Literature Review

Page: [1298 - 1368] Pages: 71

  • * (Excluding Mailing and Handling)

Abstract

Triazole is a valuable platform in medicinal chemistry, possessing assorted pharmacological properties, which could play a major role in the common mechanisms associated with various disorders like cancer, infections, inflammation, convulsions, oxidative stress and neurodegeneration. Structural modification of this scaffold could be helpful in the generation of new therapeutically useful agents. Although research endeavors are moving towards the growth of synthetic analogs of triazole, there is still a lot of scope to achieve drug discovery break-through in this area. Upcoming therapeutic prospective of this moiety has captured the attention of medicinal chemists to synthesize novel triazole derivatives. The authors amalgamated the chemistry, synthetic strategies and detailed pharmacological activities of the triazole nucleus in the present review. Information regarding the marketed triazole derivatives has also been incorporated. The objective of the review is to provide insights to designing and synthesizing novel triazole derivatives with advanced and unexplored pharmacological implications.

Keywords: 1, 2, 3-Triazole, 1, 2, 4-triazole, pharmacological activities, anti-tumor, antimicrobial, clinical indications.

Graphical Abstract

[1]
Namratha, B.; Santosh, L.G. 1,2,4-Triazoles: Synthetic strategies and pharmacological profiles. Intl. J. Pharm. Pharm. Sci., 2014, 6(8), 73-80.
[2]
Zhou, C.H.; Wang, Y. Recent researches in triazole compounds as medicinal drugs. Curr. Med. Chem., 2012, 19(1), 239-280.
[3]
Maddila, S.; Pagadala, R.; Jonnalagadda, S.B. 1,2,4-Triazoles: A review of synthetic approaches and the biological activity. Lett. Org. Chem., 2013, 10(10), 693-714.
[4]
Khrab, R.K.; Sharma, P.C. Shahar, Yar M. Pharmacological significance of triazole scaffold. J. Enzyme Inhib. Med. Chem., 2011, 26(1), 1-21.
[5]
Siddiqui, N.; Ahsan, W.; Alam, M.S.; Ali, R.; Jain, S.; Azad, B.; Akhtar, J. Triazoles: As potential bioactive agents. Intl. J. Pharm. Sci. Rev. Res., 2011, 8(1), 161-169.
[6]
Wahi, K.; Singh, A. Triazole: Recent development and biological activities. AJBPR, 2011, 2(1), 193-205.
[7]
Chen, M.D.; Lu, S.J.; Yuag, G.P.; Yang, S.Y.; Du, X.L. Synthesis and antimicrobial activity of some heterocyclic β-enamino ester derivatives with 1,2,3-triazole. Heterocycl. Commun., 2000, 6(1), 421-426.
[8]
Sherement, E.A.; Tomanov, R.I.; Trukhin, E.V.; Berestovitskaya, V.M. Synthesis of 4-aryl-5-nitro-1,2,3-triazoles. Russ. J. Org. Chem., 2004, 40(1), 594-595.
[9]
Hafez, H.N.; Abbas, H.A.; El-Gazzar, A.R. Synthesis and evaluation of analgesic, anti-inflammatory and ulcerogenic activities of some triazolo- and 2-pyrazolyl-pyrido[2,3-d]-pyrimidines. Acta Pharm., 2008, 58(1), 359-378.
[10]
Banu, K.M.; Dinaker, A.; Ananthnarayan, C. Synthesis, characterization of antimicrobial studies and pharmacological screening of some substituted 1,2,3-triazoles. Indian J. Pharm. Sci., 1999, 61(1), 202-205.
[11]
Guan, L.P.; Jin, Q.H.; Tian, G.R.; Chai, K.Y.; Quan, Z.S. Synthesis of some quinoline-2(1H)-one and 1,2,4-triazolo [4,3-a] quinoline derivatives as potent anticonvulsants. J. Pharm. Pharm. Sci., 2007, 10(3), 254-262.
[12]
Passannanti, A.; Diana, P.; Barraja, P.; Mingooia, F.; Lauria, A.; Cirrincine, G. Pyrrolo[2,3-d] [1,2,3] triazoles as potential antineoplastic agents. Heterocycles, 1998, 48(1), 1229-1235.
[13]
Gujjar, R.; Marwaha, A.; White, J.; White, L.; Creason, S.; Shackleford, D.M.; Baldwin, J.; Charman, W.N.; Buckner, F.S.; Charman, S.; Rathod, P.K.; Phillips, M.A. Identification of a metabolically stable triazolopyrimidine based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice. J. Med. Chem., 2009, 52(7), 1864-1872.
[14]
Johns, B.A.; Weatherhead, J.G.; Allen, S.H.; Thompson, J.B.; Garvey, E.P.; Foster, S.A. The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors Part 1: Establishing the pharmacophore. Bioorg. Med. Chem. Lett., 2009, 19(1), 1802-1806.
[15]
Manfredini, S.; Vicentini, C.B.; Manfrini, M.; Bianchi, N.; Rustigliano, C.; Mischiati, C.; Gambari, R. Pyrazolo-triazoles as light DNA cleavingagents. Bioorg. Med. Chem., 2000, 8(1), 2343-2346.
[16]
Duran, A.; Dogan, H.N.; Rollas, H. Synthesis and preliminary anticancer activity of new 1,4-dihydro-3-(3-hydroxy-2-naphthyl)-4-substituted-5H-1,2,4-triazoline-5-thiones. Farmaco, 2002, 57(4), 559-564.
[17]
Ameri, A.; Khodarahmi, G.; Hassanzadeh, F.; Forootanfar, H.; Hakimelahi, G.H. Novel aldimine-type Schiff bases of 4-amino-5-[(3,4,5-trimethoxyphenyl) methyl]-1,2,4-triazole-3-thione/thiol: Docking study, synthesis, biological evaluation, and anti-tubulin activity. Archiv. Der. Pharmazie, 2016, 349(8), 662-681.
[18]
Bird, C.W. A new aromaticity index and its application to five-membered ring heterocycle. Tetrahedron, 1985, 41(7), 1409-1414.
[19]
Li, J.J. Heterocyclic Chemistry in Drug Discovery; Published by Wiley, 2013, pp. 373-380.
[20]
Buzykin, B.I.; Mironova, E.V.; Nabiullin, V.N.; Gubaidullin, A.T.; Litvinov, I.A. Tautomerism of aza cycles: I. Structure of 3(5)-butylsulfanyl-5(3)-methyl(phenyl)-1H-1,2,4-triazole tautomers in crystal. Preference of the 3-RA-5-RD-1H-tautomer of 3(5)-mono-and 3,5-disubstituted 1,2,4-triazoles. Russ. J. Gen. Chem., 2006, 76(9), 1471-1486.
[21]
Kolb, H.C.; Sharpless, K.B. The growing impact of clickchemistry on drug discovery. Drug Discov. Today, 2003, 8(24), 1128-1137.
[22]
Wamhoff, H. 1,2,3-Triazoles and their benzo derivatives. In: Katritzky, A. R.; Rees, S. W.; Scriven, E. F. V. Comprehensive heterocyclic chemistry; Pergamon, Oxford, 1996; 4, pp. (1)669-732.
[23]
Tome, A.C. A review. Methods to prepare 1,2,3-triazoles are reviewed including cyclization, aromatization, ring transformation and substituent modification. Sci. Synth., 2004, 13(1), 415-601.
[24]
Kosmrly, J. Click triazoles; Springer: New York, 2012, pp. 1-236.
[25]
Krivopalov, V.P.; Shkurko, O.P. 1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring. Russ. Chem. Rev., 2005, 74(4), 339-379.
[26]
Benson, F.R.; Savell, W.L. The chemistry of the vicinal triazoles. Chem. Rev., 1948, 46(1), 1-68.
[27]
Alvarez-Builla, J.; Vaquero, J.J.; Barluenga, J. Five-Membered Heterocycles with Three Heteroatoms: Triazoles, Modern Heterocyclic Chemistry. Wiley, Weinheim 2011, 4(1), 989-1008.
[28]
Liu, Y.; Yan, W.; Chen, Y.; Petersen, J.L.; Shi, X. Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via post-triazole arylation. Org. Lett., 2008, 10(23), 5389-5392.
[29]
Yan, W.; Wang, Q.; Lin, Q.; Li, M.; Petersen, J.L.; Shi, X. N-2-Aryl-1,2,3-triazoles: A novel class of UV/blue-light-emitting fluorophores with tunable optical properties. Chem. Eur. J., 2011, 1(18), 5011-5018.
[30]
Godhani, R.D.; Jogel, A.A.; Sanghani, A.M.; Mehta, J.P. Synthesis and biological screening of 1,2,4-triazole derivatives. Indian J. Chem., 2015, 54B, 556-564.
[31]
Shelke, G.M.; Rao, V.K.; Jha, M.; Cameron, T.S.; Kumar, A. Microwave-assisted catalyst-free synthesis of substituted 1,2,4-triazoles. Synlet, 2015, 26(1), 404-407.
[32]
Tam, A.; Armstrong, I.S.; La Cruz, T.E. Multicomponent synthesis of 1-aryl 1,2,4-triazoles. Org. Lett., 2013, 15(1), 3585-3589.
[33]
Ueda, S.; Nagasawa, H. Facile synthesis of 1,2,4-triazoles via a copper-catalyzed tandemaddition-oxidative cyclization. J. Am. Chem. Soc., 2009, 131(42), 15080-15081.
[34]
Huang, H.; Guo, W.; Wu, W.; Li, C.J.; Jiang, H. Copper-catalyzed oxidative C(sp3)-H functionalization for facilesynthesis of 1,2,4-triazoles and 1,3,5-triazines from amidines. Org. Lett., 2015, 17(12), 2894-2897.
[35]
Gogoi, A.; Guin, S.; Rajamanickam, S.; Rout, S.K.; Patel, B.K.J. Synthesis of 1,2,4-triazoles via oxidative heterocyclization: Selective C-N bond over C-S bond formation. J. Org. Chem., 2015, 80(18), 9016-9027.
[36]
Castanedo, G.M.; Seng, P.S.; Blaquiere, N.; Trapp, S.; Staben, S.T. Rapid synthesis of 1,3,5-substituted 1,2,4-triazolesfrom carboxylic acids, amidines, and hydrazines. J. Org. Chem., 2011, 76(4), 1177-1179.
[37]
Bechara, W.S.; Khazhieva, I.S.; Rodriguez, E.; Charette, A.B. One-pot synthesis of 3,4,5-trisubstituted 1,2,4-triazoles via the addition of hydrazides to activated secondary amides. Org. Lett., 2015, 17(5), 1184-1187.
[38]
Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P.; Vidavalur, S. A simple and efficient synthesis of 3,4,5-trisubstituted/N-fused1,2,4-triazoles via ceric ammonium nitrate catalyzed oxidative cyclization of amidrazones with aldehydes using polyethylene glycol as a recyclable reaction medium. Synthesis, 2015, 47(4), 517-525.
[39]
Wang, L.Y.; Tseng, W.C.; Lin, H.Y.; Wong, F.F. An effective nitrilimine cycloaddition for the synthesis of 1,3,5-trisubstituted-1,2,4-triazoles from oximes with hydrazonoyl hydrochlorides. Synlet, 2011, 10(1), 1467-1471.
[40]
Xu, Y.; McLaughlin, M.; Bolton, E.N.; Reamer, R.A. Practical synthesis of functionalized 1,5-disubstituted 1,2,4-triazole derivatives. J. Org. Chem., 2010, 75(24), 8666-8669.
[41]
Batchelor, D.V.; Beal, D.M.; Brown, T.B.; Ellis, D.; Gordon, D.W.; Johnson, P.S.; Mason, H.J.; Ralph, M.J.; Underwood, T.J.; Wheeler, S. A convenient synthesis of highly substituted 3-N,N-dialkylamino-1,2,4-triazoles. Synlett, 2008, 16, 2421-2424.
[42]
Wong, B.; Stumpf, A.; Carrera, D.; Gu, C.; Zhang, H. A safe synthesis of 1,5-disubstituted 3-amino-1H-1,2,4-triazoles from 1,3,4-oxadiazolium hexafluorophosphates. Synthesis, 2013, 45(8), 1083-1093.
[43]
Yin, P.; Ma, W.B.; Chen, Y.; Huang, W.C.; Deng, Y.; He, L. Highly efficient cyanoimidation of aldehydes. Org. Lett., 2009, 11(23), 5482-5485.
[44]
Haider, S.; Alam, M.S.; Hamid, H. 1,2,3-Triazoles: Scaffold with medicinal significance. Inflamm. Cell Signal., 2014, 1(1)e95
[45]
Agalave, S.G.; Maujan, S.R.; Pore, V.S. Click chemistry: 1,2,3-Triazoles as pharmacophores. Chem. Asian J., 2011, 6(10), 2696-2718.
[46]
Almasirad, A.; Tabatabai, S.A.; Faizi, M.; Kebriaeezadeh, A.; Mehrabi, N.; Dalvandi, A.; Shafiee, A. Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy) phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg. Med. Chem. Lett., 2004, 14(24), 6057-6059.
[47]
Amir, M.; Shikha, K. Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl] acetic acid derivatives. Eur. J. Med. Chem., 2004, 39(6), 535-545.
[48]
Holla, B.S.; Poojary, K.N.; Rao, B.S.; Shivananda, M.K. New bis-aminomercapto triazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur. J. Med. Chem., 2002, 37(6), 511-517.
[49]
Kumar, S.S.; Kavitha, H.P. Synthesis and biological applications of triazole derivatives - A review. Mini Rev. Org. Chem., 2013, 10(1), 40-65.
[50]
Manclus, J.J.; Moreno, M.J.; Plana, E.; Montoya, A. Development of monoclonal immune assays for the determination of triazole fungicides in fruit juices. J. Agric. Food Chem., 2008, 56(1), 8793-8800.
[51]
Masuda, K.; Toga, T.; Hayashi, N. Synthesis of 3-morpholino-N-ethoxycarbonyl sydnonimine-5-14C (sin-10-14C). J. Label Compd., 1975, 11(2), 301-304.
[52]
Pingaew, R.; Mandi, P.; Nantasenamat, C.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity. Eur. J. Med. Chem., 2014, 81(1), 192-203.
[53]
Pingaew, R.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzene sulfonamides. Med. Chem. Res., 2014, 23, 1768-1780.
[54]
Pingaew, R.; Prachayasittikul, V.; Mandi, P.; Nantasenamat, C.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors. Bioorg. Med. Chem., 2015, 23(13), 3472-3480.
[55]
Prachayasittikul, V.; Pingaew, R.; Worachartcheewan, A.; Nantasenamat, C.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives. Eur. J. Med. Chem., 2014, 84(1), 247-263.
[56]
Prasad, D.J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B.S.; Kumari, N.S. Synthesis and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety. Eur. J. Med. Chem., 2009, 44(2), 551-557.
[57]
Holla, B.S.; Gonsalves, R.; Shenoy, S. Studies on some N-bridged heterocycles derived from bis-[4-amino5-mercapto-1,2,4-triazol-3-yl] alkanes. II Farmaco, 1998, 53(8-9), 574-578.
[58]
Holla, B.S.; Veerendra, B.; Shivananda, M.K.; Poojary, B. Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. Eur. J. Med. Chem., 2013, 38(7-8), 759-767.
[59]
Avula, S.; Madavarapu, S.; Malladi, S.; Pulluri, K.; Kontham, S.; Vasumathi, R.K. Synthesis and biological evaluation of triazole linked thiazolidenone glycosides. Acta Chim. Slov., 2016, 63(4), 827-836.
[60]
Vatmurge, N.S.; Hazra, B.G.; Pore, V.S.; Shirazi, F.; Chavan, P.S.; Deshpande, M.V. Synthesis and antimicrobial activity of β-lactam-bile acid conjugates linked via triazole. Bioorg. Med. Chem. Lett., 2008, 18(6), 2043-2047.
[61]
Jin, C.; Liang, Y.J.; He, H.; Fu, L. Synthesis and antitumor activity of ureas containing pyrimidinyl group. Eur. J. Med. Chem., 2011, 46(1), 429-432.
[62]
Zhu, S.L.; Wu, Y.; Liu, C.J.; Wei, C.Y.; Tao, J.C.; Liu, H.M. Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents. Eur. J. Med. Chem., 2013, 65(1), 70-82.
[63]
Paci, A.; Veal, G.; Bardin, C.; Leveque, D.; Widmer, N.; Beijnen, J.; Astier, A.; Chatelut, E. Review of therapeutic drug monitoring of anticancer drugs part 1-Cytotoxics. Eur. J. Cancer, 2014, 50(12), 2010-2019.
[64]
Chandrashekhar, M.; Nayak, V.L.; Ramakrishna, S.; Mallavadhani, U.V. Novel triazole hybrids of myrrhanone C, a natural polypodane triterpene: Synthesis, cytotoxic activity and cell based studies. Eur. J. Med. Chem., 2016, 114(23), 293-307.
[65]
Dangroo, N.A.; Singh, J.; Dar, A.A.; Gupta, N.; Chinthakindi, P.K.; Kaul, A.; Khuroo, M.A.; Sangwan, P.L. Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation. Eur. J. Med. Chem., 2016, 120(1), 160-169.
[66]
El-Sherief, H.A.M.; Youssif, B.G.M.; Bukhari, S.A.N.; Abdel-Aziz, M.; Abdel-Rahman, H.M. Novel 1,2,4-triazole derivatives as potential anticancer agents: Design, synthesis, molecular docking and mechanistic studies. Bioorg. Chem., 2017, 76(1), 314-325.
[67]
Gregoric, T.; Sedic, M.; Grbcic, P.; Paravic, A.T.; Pavelic, S.K.; Cetina, M.; Vianello, R.; Raic-Malic, S. Novel pyrimidine-2,4-dione-1,2,3-triazole and furo[2,3-d] pyrimidine-2-one-1,2,3-triazole hybrids as potential anti-cancer agents: Synthesis, computational and X-ray analysis and biological evaluation. Eur. J. Med. Chem., 2017, 125(5), 1247-1267.
[68]
Hou, W.; Luo, Z.; Zhang, G.; Cao, D.; Li, D.; Ruan, H.; Ruan, B.H.; Su, L.; Xu, H. Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids. Eur. J. Med. Chem., 2017, 138(1), 1042-1052.
[69]
Hussaini, S.M.; Yedla, P.; Babu, K.S.; Shaik, T.B.; Chityal, G.K.; Kamal, A. Synthesis and biological evaluation of 1,2,3-triazole tethered pyrazoline and chalcone derivatives. Chem. Biol. Drug Des., 2016, 88(1), 97-109.
[70]
Kraljevic, T.G.; Harej, A.; Sedic, M.; Pavelic, S.K.; Stepanic, V.; Drenjancevic, D.; Talapko, J.; Raic-Malic, S. Synthesis, in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazole-coumarin hybrids. Eur. J. Med. Chem., 2016, 124(1), 794-808.
[71]
Kulabas, N.; Tatar, E.; Ozakpinar, O.B.; Ozsavci, O.; Pannecouque, C.; Clercq, E.D.; Kucukguzel, I. Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells. Eur. J. Med. Chem., 2016, 121(1), 58-70.
[72]
Liu, C.F.; Shen, Q.K.; Li, J.J.; Tian, Y.S.; Quan, Z. Synthesis and biological evaluation of novel 7-hydroxy-4-phenylchromen-2-one-linked to triazole moieties as potent cytotoxic agents. J. Enzyme Inhib. Med. Chem., 2017, 32(1), 1111-1119.
[73]
Mandalapu, D.; Saini, K.S.; Gupta, S.; Sharma, V.; Malik, M.Y.; Chaturvedi, S.; Bala, V.; Hamidullah, T.S.; Maikhuri, J.P.; Wahajuddin, M.; Konwar, R.; Gupta, G.; Sharma, V.L. Synthesis and biological evaluation of some novel triazole hybrids of curcumin mimics and their selective anticancer activity against breast and prostate cancer cell lines. Bioorg. Med. Chem. Lett., 2016, 26(17), 4223-4232.
[74]
Mareddy, J.; Suresh, N.; Kumar, C.G.; Kapavarapu, R.; Jayasree, A.; Pal, S. 1,2,3-Triazole-nimesulide hybrid: Their design, synthesis and evaluation as potential anticancer agents. Bioorg. Med. Chem. Lett., 2017, 27(3), 518-523.
[75]
Milosev, M.Z.; Jakovljevic, K.; Joksovic, M.D.; Stanojkovic, T.; Matic, I.J.; Perovic, M.; Tesic, V.; Kanazir, S.; Mladenovic, M.; Rodic, M.V.; Leovac, V.M.; Trifunovic, S.; Markovic, V. Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies. Chem. Biol. Drug Des., 2017, 89(6), 943-952.
[76]
Mioc, M.; Soica, C.; Bercean, V.; Avram, S.; Balan-Porcarasu, M.; Coricovac, D.; Ghiulai, R.; Muntean, D.; Andrica, F.; Dehelean, C.; Spandidos, D.A.; Tsatsakis, A.M.; Kurunczi, L. Design, synthesis and pharmaco-toxicological assessment of 5-mercapto-1,2,4-triazole derivatives with antibacterial and antiproliferative activity. Int. J. Oncol., 2017, 50(4), 1175-1183.
[77]
Murty, M.S.; Katiki, M.R.; Nanubolu, J.B.; Garimella, S.; Polepalli, S.; Jain, N.; Buddana, S.K.; Prakasham, R.S. Synthesis and biological evaluation of novel tamoxifen-1,2,4-triazole conjugates. Mol. Divers., 2016, 20(3), 687-703.
[78]
Nagarsenkar, A.; Guntuku, L.; Guggilapu, S.D.; Danthi, B.K.; Gannoju, S.; Naidu, V.G.M.; Bathini, N.B. Synthesis and apoptosis inducing studies of triazole linked 3-benzylidene isatin derivatives. Eur. J. Med. Chem., 2016, 124(41), 782-793.
[79]
Kumar, R.N.; Dev, G.J.; Ravikumar, N.; Swaroop, D.K.; Debanjan, B.; Bharath, G.; Narsaiah, B.; Jain, N.; Rao, A.G. Synthesis of novel triazole/isoxazole functionalized 7-(trifluoromethyl)pyrido[2,3-d]pyrimidine derivatives as promising anticancer and antibacterial agents. Bioorg. Med. Chem. Lett., 2016, 26(12), 2927-2930.
[80]
Rao, A.V.S.; Swapna, K.; Shaik, S.P.; Nayak, V.L.; Reddy, T.S.; Sunkari, S.; Shaik, T.B.; Bagul, C.; Kamal, A. Synthesis and biological evaluation of cis-restricted triazole/tetrazole mimics of combretastatin-benzothiazole hybrids as tubulin polymerization inhibitors and apoptosis inducers. Bioorg. Med. Chem., 2017, 25(3), 977-999.
[81]
Ye, W.; Yao, Q.; Yu, S.; Gong, P.; Qin, M. Synthesis and antitumor activity of triazole-containing sorafenib analogs. Molecules, 2017, 22(10), 1759-1770.
[82]
Zhang, S.Y.; Fu, D.J.; Yue, X.X.; Liu, Y.C.; Song, J.; Sun, H.H.; Liu, H.M.; Zhang, Y.B. Design, synthesis and structure-activity relationships of novel chalcone-1,2,3-triazole-azole derivates as antiproliferative agents. Molecules, 2016, 21(5), 653-664.
[83]
Zhao, P.L.; Chen, P.; Li, Q.; Hu, M.J.; Diao, P.C.; Pan, E.S.; You, W.W. Design, synthesis and biological evaluation of novel 3-alkylsulfanyl-4-amino-1,2,4-triazole derivatives. Bioorg. Med. Chem. Lett., 2016, 26(15), 3679-3683.
[84]
Zi, C.T.; Xu, F.Q.; Li, G.T.; Li, Y.; Ding, Z.T.; Zhou, J.; Jiang, Z.H.; Hu, J.M. Synthesis and anticancer activity of glucosylated podophyllotoxin derivatives linked via 4β-triazole rings. Molecules, 2013, 18(11), 13992-14012.
[85]
Zou, Y.; Zhao, Q.; Hu, H.; Hu, L.; Yu, S.; Xu, M.; Wu, Q. Synthesis and in vitro antitumor activities of xanthone derivatives containing 1,4-disubstituted-1,2,3-triazole moiety. Arch. Pharm. Res., 2012, 35(12), 2093-2104.
[86]
Sambasiva Rao, P.; Kurumurthy, C.; Veeraswamy, B.; Santhosh, K.G.; Shanthan, R.P.; Pamanji, R.; Venkateswara, R.J.; Narsaiah, B. Synthesis of novel 2-alkyl triazole-3-alkyl substituted quinoline derivatives and their cytotoxic activity. Bioorg. Med. Chem. Lett., 2013, 23(5), 1225-1227.
[87]
Pertino, M.W.; Lopez, C.; Theoduloz, C.; Schmeda-Hirschmann, G. 1,2,3-triazole-substituted oleanolic acid derivatives: Synthesis and antiproliferative activity. Molecules, 2013, 18(7), 7661-7674.
[88]
Yan, S.J.; Liu, Y.J.; Chen, Y.L.; Liu, L.; Lin, J. An efficient one-pot synthesis of heterocycle-fused 1,2,3-triazole derivatives as anti-cancer agents. Bioorg. Med. Chem. Lett., 2010, 20(17), 5225-5228.
[89]
Zhao, P.L.; Ma, W.F.; Duan, A.N.; Zou, M.; Yan, Y.C.; You, W.W.; Wu, S.G. One-pot synthesis of novel isoindoline-1,3-dione derivatives bearing 1,2,4-triazole moiety and their preliminary biological evaluation. Eur. J. Med. Chem., 2012, 54(1), 813-822.
[90]
Parida, P.K.; Sau, A.; Ghosh, T.; Jana, K.; Biswas, K.; Raha, S.; Misra, A.K. Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents. Bioorg. Med. Chem. Lett., 2014, 24(16), 3865-3868.
[91]
Mavrova, A.; Wesselinova, D.; Tsenov, Y.A.; Denkova, P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on immunocompetent cells. Eur. J. Med. Chem., 2009, 44(1), 63-69.
[92]
Poornima, B.; Siva, B.; Shankaraiah, G.; Venkanna, A.; Nayak, V.L.; Ramakrishna, S.; Venkatrao, C.; Babu, K.S. Novel sesquiterpenes from Schisandra grandiflora: Isolation, cytotoxic activity and synthesis of their triazole derivatives using “click” reaction. Eur. J. Med. Chem., 2015, 92(1), 449-458.
[93]
Praveena, K.S.; Durgadas, S.; Suresh, B.N.; Akkenapally, S.; Ganesh, K.C.; Deora, G.S.; Murthy, N.Y.; Mukkanti, K.; Pal, S. Synthesis of 2,2,4-trimethyl-1,2-dihydroquinolinyl substituted 1,2,3-triazole derivatives: Their evaluation as potential PDE 4B inhibitors possessing cytotoxic properties against cancer cells. Bioorg. Chem., 2014, 53(1), 8-14.
[94]
Tu, G.; Yan, Y.; Chen, X.; Lv, Q.; Wang, J.; Li, S. Synthesis and antiproliferative assay of 1,3,4-oxadiazole and 1,2,4-triazole derivatives in cancer cells. Drug Discov. Ther., 2013, 7(2), 58-65.
[95]
Ratnakar Reddy, K.; Sambasiva Rao, P.; Jitender, D.G.; Poornachandra, Y.; Ganesh, K.C.; Shanthan Rao, P.; Narsaiah, B. Synthesis of novel 1,2,3-triazole/isoxazole functionalized 2H-chromene derivatives and their cytotoxic activity. Bioorg. Med. Chem. Lett., 2014, 24(7), 1661-1663.
[96]
Wei, G.; Luan, W.; Wang, S.; Cui, S.; Li, F.; Liu, Y.; Liu, Y.; Cheng, M. A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation. Org. Biomol. Chem., 2015, 13(5), 1507-1514.
[97]
Mareddy, J.; Nallapati, S.B.; Anireddy, J.; Devi, Y.P.; Mangamoori, L.N.; Kapavarapu, R.; Pal, S. Synthesis and biological evaluation of nimesulide based new class of triazole derivatives as potential PDE4B inhibitors against cancer cells. Bioorg. Med. Chem. Lett., 2013, 23(24), 6721-6727.
[98]
Pokhodylo, N.; Shyyka, O.; Matiychuk, V. Synthesis of 1,2,3-triazole derivatives and evaluation of their anticancer activity. Sci. Pharm., 2013, 81(3), 663-676.
[99]
Li, B.L.; Li, B.; Zhang, R.L.; Zhao, J.J.; Wang, X.F.; Liu, Y.M.; Shi, Y.P.; Liu, J.B.; Chen, B.Q. Synthesis and antiproliferative evaluation of novel 1,2,4-triazole derivatives incorporating benzisoselenazolone scaffold. Bioorg. Med. Chem. Lett., 2016, 26(4), 1279-1281.
[100]
Jordao, A.K.; Ferreira, V.F.; Souza, T.M.; Faria, G.G.; Machado, V.; Abrantes, J.L.; de Souza, M.C.; Cunha, A.C. Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorg. Med. Chem., 2011, 19(6), 1860-1865.
[101]
Elamari, H.; Slimi, R.; Chabot, G.G.; Quentin, L.; Scherman, D.; Girard, C. Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes. Eur. J. Med. Chem., 2013, 60, 360-364.
[102]
Sztanke, K.; Tuzimski, T.; Rzymowska, J.; Pasternak, K.; Kandefer-Szerszen, M. Synthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives. Eur. J. Med. Chem., 2008, 43(2), 404-419.
[103]
Avanzo, R.E.; Anesini, C.; Fascio, M.L.; Errea, M.I.; D’Accorso, N.B. 1,2,4-Triazole D-ribose derivatives: Design, synthesis and antitumoral evaluation. Eur. J. Med. Chem., 2012, 47(1), 104-110.
[104]
Benci, K.; Mandic, L.; Suhina, T.; Sedic, M.; Klobucar, M. Kraljevic, Pavelic, S.; Pavelic, K.; Wittine, K.; Mintas, M. Novel coumarin derivatives containing 1,2,4-triazole, 4,5-dicyanoimidazole and purine moieties: Synthesis and evaluation of their cytostatic activity. Molecules, 2012, 17(9), 11010-11025.
[105]
Chen, H.; Zuo, S.; Wang, X.; Tang, X.; Zhao, M.; Lu, Y.; Chen, L.; Liu, J.; Liu, Y.; Liu, D.; Zhang, S.; Li, T. Synthesis of 4β-triazole-podophyllotoxin derivatives by azide-alkyne cycloaddition and biological evaluation as potential antitumor agents. Eur. J. Med. Chem., 2011, 46(9), 4709-4714.
[106]
Chen, X.; Shi, Y.M.; Huang, C.; Xia, S.; Yang, L.J.; Yang, X.D. Novel dibenzo[b, d]furan-1H-1,2,4-triazole derivatives: Synthesis and antitumor activity. Anticancer. Agents Med. Chem., 2016, 16(3), 377-386.
[107]
Cui, Z.N.; Shi, Y.X.; Cui, J.R.; Ling, Y.; Li, B.J.; Yang, X.L. Synthesis and bioactivities of novel pyrazole and triazole derivatives containing 5-phenyl-2-furan. Chem. Biol. Drug Des., 2012, 79(1), 121-127.
[108]
Freitas, L.B.; Borgati, T.F.; de Freitas, R.P.; Ruiz, A.L.; Marchetti, G.M.; deCarvalho, J.E.; da Cunha, E.F.; Ramalho, T.C.; Alves, R.B. Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety. Eur. J. Med. Chem., 2014, 84(1), 595-604.
[109]
Kumbhare, R.M.; Dadmal, T.L.; Ramaiah, M.J.; Kishore, K.S. Pushpa, Valli, S.N.; Tiwari, S.K.; Appalanaidu. K.; Rao, Y.K.; Bhadra, M.P. Synthesis and anticancer evaluation of novel triazole linked N-(pyrimidin-2-yl) benzo[d]thiazol-2-amine derivatives as inhibitors of cell survival proteins and inducers of apoptosis in MCF-7 breast cancer cells. Bioorg. Med. Chem. Lett., 2015, 25(3), 654-658.
[110]
Kurumurthy, C.; Veeraswamy, B.; Sambasiva Rao, P.; Santhosh, K.G.; Shanthan Rao, P.; Loka Reddy, V.; Venkateswara Rao, J.; Narsaiah, B. Synthesis of novel 1,2,3-triazole tagged pyrazolo[3,4-b]pyridine derivatives and their cytotoxic activity. Bioorg. Med. Chem. Lett., 2014, 24(3), 746-749.
[111]
Shi, Y.J.; Song, X.J.; Li, X.; Ye, T.H.; Xiong, Y.; Yu, L.T. Synthesis and biological evaluation of 1,2,4-triazole and 1,3,4-thiadiazole derivatives as potential cytotoxic agents. Chem. Pharm. Bull., 2013, 61(11), 1099-1104.
[112]
Kharb, R.; Yar, M.S.; Sharma, P.C. New insights into chemistry and anti-infective potential of triazole scaffold. Curr. Med. Chem., 2011, 18(21), 3265-3297.
[113]
Xiao, H.; Li, P.; Hu, J.; Li, R.; Wu, L.; Guo, D. Synthesis and antibacterial activity of novel 5,5′-(pyridine-2,6-diyl) bis(4-arylideneamino-3-mercapto-1,2,4-triazole)-related derivatives. Appl. Biochem. Biotechnol., 2014, 172(4), 2188-2196.
[114]
Karaca Gencer, H.; Acar Cevik, U.; Levent, S.; Saglik, B.N.; Korkut, B.; Ozkay, Y.; Ilgin, S.; Ozturk, Y. New benzimidazole-1,2,4-triazole hybrid compounds: Synthesis, anticandidal activity and cytotoxicity evaluation. Molecules, 2017, 22(4), 507-528.
[115]
Ahmed, F.; Perveen, S.; Shah, K.; Shah, M.R.; Ahmed, S. Synthesis and characterization of triazole based supramolecule for interaction with cefuroxime in tap water and blood plasma. Ecotoxicol. Environ. Saf., 2018, 147(1), 49-54.
[116]
Aouad, M.R. Synthesis and antimicrobial screening of novel thioglycosides and acyclonucleoside analogs carrying 1,2,3-triazole and 1,3,4-oxadiazole moieties. Nucleosides Nucleotides Nucleic Acids, 2016, 35(1), 1-15.
[117]
Bakka, T.A.; Strom, M.B.; Andersen, J.H.; Gautun, O.R. Methyl propiolate and 3-butynone: Starting points for synthesis of amphiphilic 1,2,3-triazole peptidomimetics for antimicrobial evaluation. Bioorg. Med. Chem., 2017, 25(20), 5380-5395.
[118]
Cavusoglu, B.K.; Yurttas, L.; Canturk, Z. The synthesis, antifungal and apoptotic effects of triazole-oxadiazoles against Candida species. Eur. J. Med. Chem., 2017, 144(1), 255-261.
[119]
Fu, N.; Wang, S.; Zhang, Y.; Zhang, C.; Yang, D.; Weng, L.; Zhao, B.; Wang, L. Efficient click chemistry towards fatty acids containing 1,2,3-triazole: Design and synthesis as potential antifungal drugs for Candida albicans. Eur. J. Med. Chem., 2017, 136(1), 596-602.
[120]
Gonzalez-Calderon, D.; Mejia-Dionicio, M.G.; Morales-Reza, M.A. Ramirez-Villalva. A.; Morales-Rodriguez, M.; Jauregui-Rodriguez, B.; Diaz-Torres, E.; Gonzalez-Romero, C.; Fuentes-Benites, A. Azide-enolate 1,3-dipolar cycloaddition in the synthesis of novel triazole-based miconazole analogues as promising antifungal agents. Eur. J. Med. Chem., 2016, 112, 60-65.
[121]
Kant, R.; Kumar, D.; Agarwal, D.; Gupta, R.D.; Tilak, R.; Awasthi, S.K.; Agarwal, A. Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities. Eur. J. Med. Chem., 2016, 113(1), 34-49.
[122]
Kant, R.; Singh, V.; Nath, G.; Awasthi, S.K.; Agarwal, A. Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents. Eur. J. Med. Chem., 2016, 124(1), 218-228.
[123]
Liang, Z.; Xu, H.; Tian, Y.; Guo, M.; Su, X.; Guo, C. Design, synthesis and antifungal activity of novel benzofuran-triazole hybrids. Molecules, 2016, 21(6), 732-742.
[124]
Lin, G.S.; Duan, W.G.; Yang, L.X.; Huang, M.; Lei, F.H. Synthesis and antifungal activity of novel myrtenal-based 4-methyl-1,2,4-triazole-thioethers. Molecules, 2017, 22(2), 193-202.
[125]
Lopez-Rojas, P.; Janeczko, M.; Kubinski, K.; Amesty, A.; Maslyk, M.; Estevez-Braun, A. Synthesis and antimicrobial activity of 4-substituted 1,2,3-triazole-coumarin derivatives. Molecules, 2018, 23(1), 199-216.
[126]
Rezki, N.; Aouad, M.R. Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation. Acta Pharm., 2017, 67(3), 309-324.
[127]
Sadeghpour, H.; Khabnadideh, S.; Zomorodian, K.; Pakshir, K.; Hoseinpour, K.; Javid, N.; Faghih-Mirzaei, E.; Rezaei, Z. Design, synthesis, and biological activity of new triazole and nitro-triazole derivatives as antifungal agents. Molecules, 2017, 22(7), 1150-1160.
[128]
Stana, A.; Enache, A.; Vodnar, D.C.; Nastasa, C.; Benedec, D.; Ionut, I.; Login, C.; Marc, G.; Oniga, O.; Tiperciuc, B. New thiazolyl-triazole schiff bases: Synthesis and evaluation of the anti-candida potential. Molecules, 2016, 21(11), 1595-1613.
[129]
Sui, G.; Zhang, W.; Zhou, K.; Li, Y.; Zhang, B.; Xu, D.; Zou, Y.; Zhou, W. Trialkylamine Derivatives Containing a Triazole moiety as promising ergosterol biosynthesis inhibitor: Design, synthesis, and antifungal activity. Chem. Pharm. Bull. (Tokyo), 2017, 65(1), 82-89.
[130]
Unver, Y.; Deniz, S.; Celik, F.; Akar, Z.; Kucuk, M.; Sancak, K. Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities. J. Enzyme Inhib. Med. Chem., 2016, 31(Suppl. 3), 89-95.
[131]
Vijai Kumar Reddy, T.; Jyotsna, A.; Prabhavathi Devi, B.L.; Prasad, R.B.; Poornachandra, Y.; Ganesh Kumar, C. Design, synthesis and in vitro biological evaluation of short-chain C12-sphinganine and its 1,2,3-triazole analogs as potential antimicrobial and anti-biofilm agents. Eur. J. Med. Chem., 2016, 118(1), 98-106.
[132]
Wu, J.; Ni, T.; Chai, X.; Wang, T.; Wang, H.; Chen, J.; Jin, Y.; Zhang, D.; Yu, S.; Jiang, Y. Molecular docking, design, synthesis and antifungal activity study of novel triazole derivatives. Eur. J. Med. Chem., 2018, 143(1), 1840-1846.
[133]
Zhang, W.; Sui, G.; Li, Y.; Fang, M.; Yang, X.; Ma, X.; Zhou, W. Synthesis and in vitro antifungal activities of novel benzamide derivatives containing a triazole moiety. Chem. Pharm. Bull. (Tokyo), 2016, 64(6), 616-624.
[134]
Thomas, K.D.; Adhikari, A.V.; Shetty, N.S. Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety. Eur. J. Med. Chem., 2010, 45(9), 3803-3810.
[135]
Shi, Y.; Zhou, C.H. Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents. Bioorg. Med. Chem. Lett., 2011, 21(3), 956-960.
[136]
Turan-Zitouni, G.; Kaplancikli, Z.A.; Yildiz, M.T.; Chevallet, P.; Kaya, D. Synthesis and antimicrobial activity of 4-phenyl/ cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2-thiazolyl) acetamido]thio-4H-1,2,4-triazole derivatives. Eur. J. Med. Chem., 2005, 40(6), 607-613.
[137]
Upmanyu, N.; Kumar, S.; Kharya, M.D.; Shah, K.; Mishra, P. Synthesis and anti-microbial evaluation of some novel 1,2,4-triazole derivatives. Acta Pol. Pharm., 2011, 68(2), 213-221.
[138]
Popiolek, L.; Kosikowska, U.; Mazur, L.; Dobosz, M.; Malm, A. Synthesis and antimicrobial evaluation of some novel 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Med. Chem. Res., 2013, 22(7), 3134-3147.
[139]
Popiolek, L.; Kosikowska, U.; Dobosz, M.; Malm, A. Synthesis and in vitro antimicrobial activity of new 4-phenyl-5-methyl-4H-1,2,4-triazole-3-thione derivatives. J. Enzy Inhib. Med. Chem., 2013, 28(3), 479-488.
[140]
Zhang, F.; Wen, Q.; Wang, S.F.; Shahla, K.B.; Yang, Y.S.; Liu, J.J.; Zhang, W.M.; Zhu, H.L. Design, synthesis and antibacterial activities of 5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiol derivatives containing Schiff base formation as FabH inhibitory. Bioorg. Med. Chem. Lett., 2014, 24, 90-95.
[141]
Yasuda, N.; Iwagami, H.; Sasaki, Y. Synthesis and antibacterial activity of triazole and isoxazole derivatives of ampicillin. J. Antibiot., 1983, 36(11), 1516-1524.
[142]
Pandeya, S.N.; Sriram, D.; Nath, G.; de Clercq, E. Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneimittelforschung, 2000, 50(1), 55-59.
[143]
Ulusoy, N.; Gursoy, A.; Otuk, G. Synthesis and antimicrobial activity of some 1,2,4-triazole-3-mercaptoacetic acid derivatives. Farmaco, 2001, 56(12), 947-952.
[144]
Kushwaha, K.; Kaushik, N. Lata; Jain, S.C. Design and synthesis of novel 2H-chromen-2-one derivatives bearing 1,2,3-triazole moiety as lead antimicrobials. Bioorg. Med. Chem. Lett., 2014, 24(7), 1795-1801.
[145]
Li, C.; Liu, J.C.; Li, Y.R.; Gou, C.; Zhang, M.L.; Liu, H.Y.; Li, X.Z.; Zheng, C.J.; Piao, H.R. Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety. Bioorg. Med. Chem. Lett., 2015, 25(15), 3052-3056.
[146]
Koparir, M.; Orek, C.; Parlak, A.E.; Soylemez, A.; Koparir, P.; Karatepe, M.; Dastan, S.D. Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones. Eur. J. Med. Chem., 2013, 63(1), 340-346.
[147]
Ikizler, A.A.; Johansson, C.B.; Bekircan, O.; Celik, C. Synthesis and antibacterial activities of some 1,2,4-triazole derivatives. Acta Pol. Pharm., 1999, 56(4), 283-288.
[148]
Ji, D.; Lu, J.; Lu, B.; Xin, C.; Mu, J.; Li, J.; Peng, C.; Bao, X. Efficient synthesis and antimicrobial activity of some novel S-β-d-glucosides of 5-aryl-1,2,4-triazole-3-thiones derivatives. Bioorg. Med. Chem. Lett., 2013, 23(7), 1997-2000.
[149]
Eswaran, S.; Adhikari, A.V.; Shetty, N.S. Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. Eur. J. Med. Chem., 2009, 44(11), 4637-4647.
[150]
Aggarwal, N.; Kumar, R.; Dureja, P.; Khurana, J.M. Synthesis, antimicrobial evaluation and QSAR analysis of novel nalidixic acid based 1,2,4-triazole derivatives. Eur. J. Med. Chem., 2011, 46(9), 4089-4099.
[151]
Aufort, M.; Herscovici, J.; Bouhours, P.; Moreau, N.; Girard, C. Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives. Bioorg. Med. Chem. Lett., 2008, 18(3), 1195-1198.
[152]
Bektas, H.; Karaali, N.; Sahin, D.; Demirbas, A.; Karaoglu, S.A.; Demirbas, N. Synthesis and antimicrobial activities of some new 1,2,3-triazole derivatives. Molecules, 2010, 15(4), 2427-2438.
[153]
Demirayak, S.; Benkli, K.; Guven, K. Synthesis of some 3-arylamino-5-aryloxymethyl [1,2,4]triazole derivatives and their antimicrobial activity. Pharm. Acta Helv., 1998, 72(5), 285-290.
[154]
Demirayak, S.; Benkli, K.; Guven, K. Synthesis and antimicrobial activities of some 3-arylamino-5- [2-(substituted 1-imidazolyl)ethyl]-1,2,4-triazole derivatives. Eur. J. Med. Chem., 2000, 35(11), 1037-1040.
[155]
Demirbas, N.; Karaoglu, S.A.; Demirbas, A.; Sancak, K. Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4] thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo- [1,2,4]triazole derivatives. Eur. J. Med. Chem., 2004, 39(9), 793-804.
[156]
El-Sayed, W.A.; Ali, O.M.; Hathoot, M.M.; Abdel-Rahman, A.A. Synthesis and antimicrobial activity of new substituted fused 1,2,4-triazole derivatives. Z. Naturforsch. C J. Biosci., 2010, 65(1-2), 22-28.
[157]
Guzeldemirci, N.U.; Satana, D.; Kucukbasmaci, O. Synthesis, characterization, and antimicrobial evaluation of some new hydrazinecarbothioamide, 1,2,4-triazole and 1,3,4-thiadiazole derivatives. J. Enzyme Inhib. Med. Chem., 2013, 28(5), 968-973.
[158]
Varvaresou, A.; Tsantili-Kakoulidou, A.; Siatra-Papastaikoudi, T.; Tiligada, E. Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs. Arzneimittelforschung, 2000, 50(1), 48-54.
[159]
Yu, S.; Chai, X.; Hu, H.; Yan, Y.; Guan, Z.; Zou, Y.; Sun, Q.; Wu, Q. Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase. Eur. J. Med. Chem., 2010, 45(10), 4435-4445.
[160]
Xu, J.; Cao, Y.; Zhang, J.; Yu, S.; Zou, Y.; Chai, X.; Wu, Q.; Zhang, D.; Jiang, Y.; Sun, Q. Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives. Eur. J. Med. Chem., 2011, 46(7), 3142-3148.
[161]
Yu, S.; Wang, N.; Chai, X.; Wang, B.; Cui, H.; Zhao, Q.; Zou, Y.; Sun, Q.; Meng, Q.; Wu, Q. Synthesis and antifungal activity of the novel triazole derivatives containing 1,2,3-triazole fragment. Arch. Pharm. Res., 2013, 36(10), 1215-1222.
[162]
Yan, Y.; Yu, S.; Chai, X.; Hu, H.; Wu, Q. Synthesis and antifungal activity of novel triazole derivatives. Arch. Pharm. Res., 2011, 34(10), 1649-1656.
[163]
Xu, K.; Huang, L.; Xu, Z.; Wang, Y.; Bai, G.; Wu, Q.; Wang, X.; Yu, S.; Jiang, Y. Design, synthesis, and antifungal activities of novel triazole derivatives containing the benzyl group. Drug Des. Devel. Ther., 2015, 9(1), 1459-1467.
[164]
Tsuruoka, A.; Kaku, Y.; Kakinuma, H.; Tsukada, I.; Yanagisawa, M.; Nara, K.; Naito, T. Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives. Chem. Pharm. Bull., 1998, 46(4), 623-630.
[165]
Sun, Q.Y.; Xu, J.M.; Cao, Y.B.; Zhang, W.N.; Wu, Q.Y.; Zhang, D.Z.; Zhang, J.; Zhao, H.Q.; Jiang, Y.Y. Synthesis of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase (CYP51). Eur. J. Med. Chem., 2007, 42(9), 1226-1233.
[166]
Tang, R.; Jin, L.; Mou, C.; Yin, J.; Bai, S.; Hu, D.; Wu, J.; Yang, S.; Song, B. Synthesis, antifungal and antibacterial activity for novel amide derivatives containing a triazole moiety. Chem. Cent. J., 2013, 7, 30.
[167]
Sun, G.X.; Yang, M.Y.; Shi, Y.X.; Sun, Z.H.; Liu, X.H.; Wu, H.K.; Li, B.J.; Zhang, Y.G. Microwave assistant synthesis, antifungal activity and DFT theoretical study of some novel 1,2,4-triazole derivatives containing pyridine moiety. Intl. J. Mol. Sci., 2014, 15(5), 8075-8090.
[168]
Uchida, T.; Somada, A.; Kagoshima, Y.; Konosu, T.; Oida, S. Carbon analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities. Bioorg. Med. Chem. Lett., 2008, 18(24), 6538-6541.
[169]
Uchida, T.; Kagoshima, Y.; Konosu, T. Amide analogs of antifungal dioxane-triazole derivatives: Synthesis and in vitro activities. Bioorg. Med. Chem. Lett., 2009, 19(7), 2013-2017.
[170]
Zhao, Q.J.; Hu, H.G.; Li, Y.W.; Song, Y.; Cai, L.Z.; Wu, Q.Y.; Jiang, Y.Y. Design, synthesis, and antifungal activities of novel 1H-triazole derivatives based on the structure of the active site of fungal lanosterol 14α-demethylase (CYP51). Chem. Biodivers., 2007, 4(7), 1472-1479.
[171]
Zou, Y.; Zhao, Q.; Liao, J.; Hu, H.; Yu, S.; Chai, X.; Xu, M.; Wu, Q. New triazole derivatives as antifungal agents: Synthesis via click reaction, in vitro evaluation and molecular docking studies. Bioorg. Med. Chem. Lett., 2012, 22(8), 2959-2962.
[172]
Sun, N.B.; Fu, J.Q.; Weng, J.Q.; Jin, J.Z.; Tan, C.X.; Liu, X.H. Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel 1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety. Molecules, 2013, 18(10), 12725-12739.
[173]
Onkol, T.; Dogruer, D.S.; Uzun, L.; Adak, S.; Ozkan, S.; Sahin, M.F. Synthesis and antimicrobial activity of new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. J. Enzyme Inhib. Med. Chem., 2008, 23(2), 277-284.
[174]
Lima-Neto, R.G.; Cavalcante, N.N.; Srivastava, R.M. Mendonca, Junior, F.J.; Wanderley, A.G.; Neves, R.P.; dos Anjos, J.V. Synthesis of 1,2,3-triazole derivatives and in vitro antifungal evaluation on Candida strains. Molecules, 2012, 17(5), 5882-5892.
[175]
Sheng, C.; Che, X.; Wang, W.; Wang, S.; Cao, Y.; Yao, J.; Miao, Z.; Zhang, W. Structure-based design, synthesis, and antifungal activity of new triazole derivatives. Chem. Biol. Drug Des., 2011, 78(2), 309-313.
[176]
Oida, S.; Tajima, Y.; Konosu, T.; Nakamura, Y.; Somada, A.; Tanaka, T.; Habuki, S.; Harasaki, T.; Kamai, Y.; Fukuoka, T.; Ohya, S.; Yasuda, H. Synthesis and antifungal activities of R-102557 and related dioxane-triazole derivatives. Chem. Pharm. Bull., 2000, 48(5), 694-707.
[177]
Chai, X.; Zhang, J.; Hu, H.; Yu, S.; Sun, Q.; Dan, Z.; Jiang, Y.; Wu, Q. Design, synthesis, and biological evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase. Eur. J. Med. Chem., 2009, 44(5), 1913-1920.
[178]
Chen, G.; Zhou, Y.; Cai, C.; Lu, J.; Zhang, X. Synthesis and antifungal activity of benzamidine derivatives carrying 1,2,3-triazole moieties. Molecules, 2014, 19(5), 5674-5691.
[179]
Dai, Z.C.; Chen, Y.F.; Zhang, M.; Li, S.K.; Yang, T.T.; Shen, L.; Wang, J.X.; Qian, S.S.; Zhu, H.L.; Ye, Y.H. Synthesis and antifungal activity of 1,2,3-triazole phenylhydrazone derivatives. Org. Biomol. Chem., 2015, 13(2), 477-486.
[180]
Ezabadi, I.R.; Camoutsis, C.; Zoumpoulakis, P.; Geronikaki, A.; Sokovic, M.; Glamocilija, J.; Ciric, A. Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies. Bioorg. Med. Chem., 2008, 16(3), 1150-1161.
[181]
Gupta, D.; Jain, D.K. Synthesis, antifungal and antibacterial activity of novel 1,2,4-triazole derivatives. J. Adv. Pharm. Technol. Res., 2015, 6(3), 141-146.
[182]
Guan, Z.; Chai, X.; Yu, S.; Hu, H.; Jiang, Y.; Meng, Q.; Wu, Q. Synthesis, molecular docking, and biological evaluation of novel triazole derivatives as antifungal agents. Chem. Biol. Drug Des., 2010, 76(6), 496-504.
[183]
Jiang, Y.; Zhang, J.; Cao, Y.; Chai, X.; Zou, Y.; Wu, Q.; Zhang, D.; Jiang, Y.; Sun, Q. Synthesis, in vitro evaluation and molecular docking studies of new triazole derivatives as antifungal agents. Bioorg. Med. Chem. Lett., 2011, 21(15), 4471-4475.
[184]
Jubert, A.; Massa, N.E.; Tevez, L.L.; Okulik, N.B. Vibrational and theoretical studies of the non-steroidal anti-inflamatory drugs niflumic [2-3((3-trifluoromethyl) phenylamino)-3-pyridinecarboxylic acid]; diclofenac [[2-(2,6-dichlorophenyl)amino]-benzeneacetic acid] and indometacin acids. [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid]. Vib. Spectrosc., 2005, 37(1), 161-178.
[185]
Xie, W.; Chipman, D.L.; Robertson, R.L.; Erikson, D.L. Expression of mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc. Natl. Acad. Sci. USA, 1991, 88(7), 2692-2696.
[186]
Kujubu, D.A.; Fletcher, B.S.; Varnum, B.C.; Lim, R.W.; Herschman, H.R. TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue. J. Biol. Chem., 1991, 266(1), 12866-12872.
[187]
Garcia Rodriguez, L.A.; Cattaruzzi, C.; Troncon, M.G.; Agostinis, L. Risk ofhospitalization for upper gastrointestinal tract bleeding associated withketorolac, other nonsteroidal anti-inflammatory drugs, calcium antagonists, and other antihypertensive drugs. Arch. Intern. Med., 1998, 158(1), 33-39.
[188]
Grewal, A.S.; Lather, V.; Pandita, D.; Dalal, R. Synthesis, docking and anti-inflammatory activity of triazole amine derivatives as potential phosphodiesterase-4 inhibitors. Antiinflamm. Antiallergy Agents Med. Chem., 2017, 16(1), 58-67.
[189]
Mohassab, A.M.; Hassan, H.A.; Abdelhamid, D.; Abdel-Aziz, M.; Dalby, K.N.; Kaoud, T.S. Novel quinoline incorporating 1,2,4-triazole/oxime hybrids: Synthesis, molecular docking, anti-inflammatory, COX inhibition, ulceroginicity and histopathological investigations. Bioorg. Chem., 2017, 75(1), 242-259.
[190]
Tariq, S.; Alam, O.; Amir, M. Synthesis, anti-inflammatory, p38α MAP kinase inhibitory activities and molecular docking studies of quinoxaline derivatives containing triazole moiety. Bioorg. Chem., 2017, 76(1), 343-358.
[191]
Vanga, N.R.; Kota, A.; Sistla, R.; Uppuluri, M. Synthesis and anti-inflammatory activity of novel triazole hybrids of (+)-usnic acid, the major dibenzofuran metabolite of the lichen Usnea longissima. Mol. Divers., 2017, 21(2), 273-282.
[192]
Zhang, H.J.; Wang, X.Z.; Cao, Q.; Gong, G.H.; Quan, Z.S. Design, synthesis, anti-inflammatory activity, and molecular docking studies of perimidine derivatives containing triazole. Bioorg. Med. Chem. Lett., 2017, 27(18), 4409-4414.
[193]
Rajasekaran, A.; Rajagopal, K.A. Synthesis of some novel triazole derivatives as anti-nociceptive and anti-inflammatory agents. Acta Pharm., 2009, 59(3), 355-364.
[194]
Labanauskas, L.; Udrenaite, E.; Gaidelis, P.; Brukstus, A. Synthesis of 5-(2-,3- and 4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives exhibiting anti-inflammatory activity. Farmaco, 2004, 59(4), 255-259.
[195]
Rabea, S.M.; El-Koussi, N.A.; Hassan, H.Y.; Aboul-Fadl, T. Synthesis of 5-phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid derivatives of potential anti-inflammatory activity. Arch. Pharm., 2006, 339(1), 32-40.
[196]
Kumar, H.; Javed, S.A.; Khan, S.A.; Amir, M. 1,3,4-Oxadiazole/ thiadiazole and 1,2,4-triazole derivatives of biphenyl-4-yloxy acetic acid: synthesis and preliminary evaluation of biological properties. Eur. J. Med. Chem., 2008, 43(12), 2688-2698.
[197]
Sambasiva Rao, P.; Kurumurthy, C.; Veeraswamy, B.; Santhosh, K.G.; Poornachandra, Y.; Ganesh, K.C.; Vasamsetti, S.B.; Kotamraju, S.; Narsaiah, B. Synthesis of novel 1,2,3-triazole Substituted-N-alkyl/aryl nitrone derivatives, their anti-inflammatory and anticancer activity. Eur. J. Med. Chem., 2014, 80(1), 184-191.
[198]
Kim, T.W.; Yong, Y.; Shin, S.Y.; Jung, H.; Park, K.H.; Lee, Y.H.; Lim, Y.; Jung, K.Y. Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents. Bioorg. Chem., 2015, 59(1), 1-11.
[199]
Abuo-Rahma. Gel D.; Abdel-Aziz, M.; Farag, N.A.; Kaoud, T.S. Novel 1-[4-(Aminosulfonyl) phenyl]-1H-1,2,4-triazole derivatives with remarkable selective COX-2 inhibition: Design, synthesis, molecular docking, anti-inflammatory and ulcerogenicity studies. Eur. J. Med. Chem., 2014, 83(1), 398-408.
[200]
Paprocka, R.; Wiese, M.; Eljaszewicz, A.; Helmin-Basa, A.; Gzella, A.; Modzelewska-Banachiewicz, B.; Michalkiewicz, J. Synthesis and anti-inflammatory activity of new 1,2,4-triazole derivatives. Bioorg. Med. Chem. Lett., 2015, 25(13), 2664-2667.
[201]
Amir, M.; Kumar, H.; Javed, S.A. Non-carboxylic analogues of naproxen: design, synthesis, and pharmacological evaluation of some 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole derivatives. Arch. Pharm., 2007, 340(11), 577-585.
[202]
Assis, S.P.; da Silva, M.T.; de Oliveira, R.N.; Lima, V.L. Synthesis and anti-inflammatory activity of new alkyl-substituted phthalimide 1H-1,2,3-triazole derivatives. Scientif. World J., 2012, 2012(1)925925
[203]
Jiang, B.; Zeng, Y.; Li, M.J.; Xu, J.Y.; Zhang, Y.N.; Wang, Q.J.; Sun, N.Y.; Lu, T.; Wu, X.M. Design, synthesis, and biological evaluation of 1,5-diaryl-1,2,4-triazole derivatives as selective cyclooxygenase-2 inhibitors. Arch. Pharm., 2010, 343(9), 500-508.
[204]
Hussein, M.A.; Shaker, R.M.; Ameen, M.A.; Mohammed, M.F. Synthesis, anti-inflammatory, analgesic, and antibacterial activities of some triazole, triazolothiadiazole, and triazolothiadiazine derivatives. Arch. Pharm. Res., 2011, 34(8), 1239-1250.
[205]
Blennow, K.; de Leon, M.J.; Zetterberg, H. Alzheimer’s disease. Lancet, 2006, 368(1), 387-403.
[206]
Abbott, A. Dementia: A problem for our age. Nature, 2011, 475, S2-S4.
[207]
Selkoe, D.J. Resolving controversies on the pathto Alzheimer’s therapeutics. Nat. Med., 2011, 17(1), 1060-1065.
[208]
Liu, J.; Qiu, J.; Wang, M.; Wang, L.; Su, L.; Gao, J.; Gu, Q.; Xu, J.; Huang, S.L.; Gu, L.Q.; Huang, Z.S.; Li, D. Synthesis and characterization of 1H-phenanthro[9,10-d] imidazole derivatives as multifunctionalagents for treatment of Alzheimer’s disease. Biochim. Biophys. Acta, 2014, 1840(9), 2886-2903.
[209]
Colovic, M.B.; Krstic, D.Z.; Lazarevic-Pasti, T.D.; Bondzic, A.M.; Vasic, V.M. Acetylcholinesterase inhibitors: Pharmacology and toxicology. Curr. Neuropharmacol., 2013, 11(3), 315-335.
[210]
Shi, A.; Huang, L.; Lu, C.; He, F.; Li, X. Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and β-amyloid aggregation inhibitors. Bioorg. Med. Chem., 2011, 19(7), 2298-2305.
[211]
Mohammadi-Khanaposhtani, M.; Saeedi, M.; Zafarghandi, N.S.; Mahdavi, M.; Sabourian, R.; Razkenari, E.K.; Alinezhad, H.; Khanavi, M.; Foroumadi, A.; Shafiee, A.; Akbarzadeh, T. Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives. Eur. J. Med. Chem., 2015, 92(1), 799-806.
[212]
Bagheri, S.M.; Khoobi, M.; Nadri, H.; Moradi, A.; Emami, S.; Jalili-Baleh, L.; Jafarpour, F.; Homayouni, M.F.; Foroumadi, A.; Shafiee, A. Synthesis and anticholinergic activity of 4-hydroxycoumarin derivatives containing substituted benzyl-1,2,3-triazole moiety. Chem. Biol. Drug Des., 2015, 86(5), 1215-1220.
[213]
Li, J.C.; Zhang, J.; Rodrigues, M.C.; Ding, D.J.; Longo, J.P.; Azevedo, R.B.; Muehlmann, L.A.; Jiang, C.S. Synthesis and evaluation of novel 1,2,3-triazole-based acetylcholinesterase inhibitors with neuroprotective activity. Bioorg. Med. Chem. Lett., 2016, 26(16), 3881-3885.
[214]
Saeedi, M.; Safavi, M.; Karimpour-Razkenari, E.; Mahdavi, M.; Edraki, N.; Moghadam, F.H.; Khanavi, M.; Akbarzadeh, T. Synthesis of novel chromenones linked to 1,2,3-triazole ring system: Investigation of biological activities against Alzheimer’s disease. Bioorg. Chem., 2017, 70(1), 86-93.
[215]
Deng, X.Q.; Song, M.X.; Gong, G.H.; Wang, S.B.; Quan, Z.S. Synthesis and anticonvulsant evaluation of some new 6-(substituted-phenyl)thiazolo[3,2-b][1,2,4]triazole derivatives in mice. Iran. J. Pharm. Res., 2014, 13(2), 459-469.
[216]
Modzelewska-Banachiewicz, B.; Banachiewicz, J.; Chodkowska, A.; Jagiello-Wojtowicz, E.; Mazur, L. Synthesis and biological activity of new derivatives of 3-(3,4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Eur. J. Med. Chem., 2004, 39(10), 873-877.
[217]
Kucukguzel, I.; Guniz Kucukguzel, S.; Rollas, S.; Otuk-Sanis, G.; Ozdemir, O.; Bayrak, I.; Altug, T.; Stables, J.P. Synthesis of some 3-(arylalkylthio)-4-alkyl/aryl-5-(4-aminophenyl)-4H-1,2,4-triazole derivatives and their anticonvulsant activity. Farmaco, 2004, 59(11), 893-901.
[218]
Shaikh, M.H.; Subhedar, D.D.; Nawale, L.; Dhiman, S.; Khan, F.A.K.; Sangshetti, J.N.; Shingate, B.B. 1,2,3-Triazole derivatives as antitubercular agents: Synthesis, biological evaluation and moleculardocking study. MedChemComm, 2015, 6(1), 1104-1116.
[219]
Young, D.B.; Perkins, M.D.; Duncan, K.; Barry, C.E. Confronting the scientific obstacles to global control of tuberculosis. J. Clin. Invest., 2008, 118(4), 1255-1265.
[220]
Christian, L.; Andrew, V.; Raviglione, M.C. New drugs and new regimens for the treatment of tuberculosis: Review of the drug development pipeline and implications for national programmes. Curr. Opin. Pulm. Med., 2010, 16(1), 186-193.
[221]
Sankar, M.M.; Singh, J.; Diana, S.C.; Singh, S. Molecular characterizationof Mycobacterium tuberculosis isolates from north Indian patients with extrapulmonary tuberculosis. Tuberculosis, 2013, 93(1), 75-83.
[222]
Amaroju, S.; Srinivasarao, S.; Napiorkowska, A.; Augustynowicz-Kopec, E.; Alvala, M.; Lherbet, C.; Chandra Sekhar, K.V.G. Design, synthesis of 9H-fluorenone based 1,2,3-triazole analogues as Mycobacterium tuberculosis InhA inhibitors. Chem. Biol. Drug Des., 2017.
[http://dx.doi.org/10.1111/cbdd.13127]
[223]
Aziz Ali, A.; Gogoi, D.; Chaliha, A.K.; Buragohain, A.K.; Trivedi, P.; Saikia, P.J.; Gehlot, P.S.; Kumar, A.; Chaturvedi, V.; Sarma, D. Synthesis and biological evaluation of novel 1,2,3-triazole derivatives as anti-tubercular agents. Bioorg. Med. Chem. Lett., 2017, 27(16), 3698-3703.
[224]
Sajja, Y.; Vanguru, S.; Vulupala, H.R.; Bantu, R.; Yogeswari, P.; Sriram, D.; Nagarapu, L. Design, synthesis and in vitro anti-tuberculosis activity of benzo[6,7]cyclohepta[1,2-b]pyridine-1,2,3-triazole derivatives. Bioorg. Med. Chem. Lett., 2017, 27(23), 5119-5121.
[225]
Sonawane, A.D.; Rode, N.D.; Nawale, L.; Joshi, R.R.; Joshi, R.A.; Likhite, A.P.; Sarkar, D. Synthesis and biological evaluation of 1,2,4-triazole-3-thione and 1,3,4-oxadiazole-2-thione as antimycobacterial agents. Chem. Biol. Drug Des., 2017, 90(2), 200-209.
[226]
Xu, Z.; Song, X.F.; Hu, Y.Q.; Qiang, M.; Lv, Z.S. Azide-alkyne cycloaddition towards 1H-1,2,3-triazole-tethered gatifloxacin and isatin conjugates: Design, synthesis and in vitro anti-mycobacterial evaluation. Eur. J. Med. Chem., 2017, 138(1), 66-71.
[227]
Xu, Z.; Zhang, S.; Song, X.; Qiang, M.; Lv, Z. Design, synthesis and in vitro anti-mycobacterial evaluation of gatifloxacin-1H-1,2,3-triazole-isatin hybrids. Bioorg. Med. Chem. Lett., 2017, 27(16), 3643-3646.
[228]
Yan, X.; Lv, Z.; Wen, J.; Zhao, S.; Xu, Z. Synthesis and in vitro evaluation of novel substituted isatin-propylene-1H-1,2,3-triazole-4-methylene-moxifloxacin hybrids for their anti-mycobacterial activities. Eur. J. Med. Chem., 2018, 143(1), 899-904.
[229]
Upadhayaya, R.S.; Kulkarni, G.M.; Vasireddy, N.R.; Vandavasi, J.K.; Dixit, S.S.; Sharma, V.; Chattopadhyaya, J. Design, synthesis and biological evaluation of novel triazole, urea and thiourea derivatives of quinoline against Mycobacterium tuberculosis. Bioorg. Med. Chem., 2009, 17(13), 4681-4692.
[230]
Kumar, D.; Beena Khare, G.; Kidwai, S.; Tyagi, A.K.; Singh, R.; Rawat, D.S. Synthesis of novel 1,2,3-triazole derivatives of isoniazid and them in vitro and in vivo antimycobacterial activity evaluation. Eur. J. Med. Chem., 2014, 81(1), 301-313.
[231]
Klimesova, V.; Zahajska, L.; Waisser, K.; Kaustova, J.; Mollmann, U. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives. Farmaco, 2004, 59(4), 279-288.
[232]
Tehrani, K.H.; Mashayekhi, V.; Azerang, P.; Minaei, S.; Sardari, S.; Kobarfard, F. Synthesis and antimycobacterial activity of some triazole Derivatives-New route to functionalized triazolopyridazines. Iran. J. Pharm. Res., 2015, 14(Suppl.), 59-68.
[233]
Patel, N.B.; Khan, I.H. Synthesis of 1,2,4-triazole derivatives containing benzothiazoles as pharmacologically active molecule. J. Enzyme Inhib. Med. Chem., 2011, 26(4), 527-534.
[234]
Shaikh, M.H.; Subhedar, D.D.; Arkile, M.; Khedkar, V.M.; Jadhav, N.; Sarkar, D.; Shingate, B.B. Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent. Bioorg. Med. Chem. Lett., 2016, 26(2), 561-569.
[235]
Costa, M.S.; Boechat, N.; Rangel, E.A. da Silva, Fde.C.; de Souza, A.M.; Rodrigues, C.R.; Castro, H.C.; Junior, I.N.; Lourenco, M.C.; Wardell, S.M.; Ferreira, V.F. Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives. Bioorg. Med. Chem., 2006, 14(24), 8644-8653.
[236]
Dabak, K.; Sezer, O.; Akar, A.; Anac, O. Synthesis and investigation of tuberculosis inhibition activities of some 1,2,3-triazole derivatives. Eur. J. Med. Chem., 2003, 38(2), 215-218.
[237]
Kaplancikli, Z.A.; Turan-Zitouni, G.; Chevallet, P. Synthesis and antituberculosis activity of new 3-alkylsulfanyl-1,2,4-triazole derivatives. J. Enzyme Inhib. Med. Chem., 2005, 20(2), 179-182.
[238]
Menendez, C.; Gau, S.; Lherbet, C.; Rodriguez, F.; Inard, C.; Pasca, M.R.; Baltas, M. Synthesis and biological activities of triazole derivatives as inhibitors of InhA and antituberculosis agents. Eur. J. Med. Chem., 2011, 46(11), 5524-5531.
[239]
Menendez, C.; Chollet, A.; Rodriguez, F.; Inard, C.; Pasca, M.R.; Lherbet, C.; Baltas, M. Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents. Eur. J. Med. Chem., 2012, 52(1), 275-283.
[240]
Shaikh, M.H.; Subhedar, D.D.; Khan, F.A.K.; Sangshetti, J.N.; Shingate, B.B. 1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents. Chin. Chem. Lett., 2016, 27(1), 295-301.
[241]
Sun, J.; Ding, W.X.; Zhang, K.Y.; Zou, Y. Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives. Chin. Chem. Lett., 2011, 22(1), 667-670.
[242]
Gutteridge, J.M.C.; Halliwell, B. Invited review free radicals in disease processes: a compilation of cause and consequence. Free Radic. Res. Commun., 1993, 19(1), 141-158.
[243]
Patel, R.M.; Patel, N.J. In vitro antioxidant activity of coumarin compounds byDPPH, super oxide and nitric oxide free radical scavenging methods. J. Adv. Pharm. Technol. Res., 2011, 1, 52-68.
[244]
Ashok, D.; Gundu, S.; Aamate, V.K.; Devulapally, M.G. Microwave-assisted synthesis, antioxidant and antimicrobial evaluation of 2-indolinone-based bis-1,2,3-triazole derivatives. Mol. Divers., 2018, 22(1), 57-70.
[245]
Karrouchi, K.; Chemlal, L.; Taoufik, J.; Cherrah, Y.; Radi, S.; El Abbes Faouzi, M.; Ansar, M. Synthesis, antioxidant and analgesic activities of Schiff bases of 4-amino-1,2,4-triazole derivatives containing a pyrazole moiety. Ann. Pharm. Fr., 2016, 74(6), 431-438.
[246]
Tan, W.; Li, Q.; Li, W.; Dong, F.; Guo, Z. Synthesis and antioxidant property of novel 1,2,3-triazole-linked starch derivatives via ‘click chemistry’. Intl. J. Biol. Macromol., 2016, 82, 404-410.
[247]
Sokmen, B.B.; Gumrukcuoglu, N.; Ugras, S.; Ugras, H.I.; Yanardag, R. Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new methoxy substitued bis-1,2,4-triazole derivatives. J. Enzyme Inhib. Med. Chem., 2013, 28(1), 72-77.
[248]
Kus, C.; Ayhan-Kilcigil, G.; Ozbey, S.; Kaynak, F.B.; Kaya, M.; Coban, T.; Can-Eke, B. Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Bioorg. Med. Chem., 2008, 16(8), 4294-4303.
[249]
Franklin, S.S.; Wong, N.D. Hypertension and cardiovascular disease: contributions of the Framingham heart study. Glob. Heart, 2013, 8(1), 49-57.
[250]
Zhuang, X.D.; Liao, L.Z.; Dong, X.B.; Hu, X.; Guo, Y.; Du, Z.M.; Liao, X.X.; Wang, L.C. Design, synthesis, and antihypertensive activity of curcumin-inspired compounds via ACE inhibition and vasodilation, along with a bioavailability study for possible benefit in cardiovascular diseases. Drug Des. Devel. Ther., 2016, 10(1), 129-139.
[251]
Siddiqui, A.A.; Mishra, R.; Shaharyar, M.; Husain, A.; Rashid, M.; Pal, P. Triazole incorporated pyridazinones as a new class of antihypertensiveagents: Design, synthesis and in vivo screening. Bioorg. Med. Chem. Lett., 2011, 21(1), 1023-1026.
[252]
Liu, J.; Liu, Q.; Yang, X.; Xu, S.; Zhang, H.; Bai, R.; Yao, H.; Jiang, J.; Shen, M.; Wu, X.; Xu, J. Design, synthesis, and biological evaluation of 1,2,4-triazole bearing 5-substituted biphenyl-2-sulfonamide derivatives as potential antihypertensive candidates. Bioorg. Med. Chem., 2013, 21(24), 7742-7751.
[253]
Okazaki, T.; Suga, A.; Watanabe, T.; Kikuchi, K.; Kurihara, H.; Shibasaki, M.; Fujimori, A.; Inagaki, O.; Yanagisawa, I. Studies on nonpeptide angiotensin II receptor antagonists. II. Synthesis and biological evaluation of 5H-pyrazolo[1,5-b] [1,2,4]triazole derivatives with a C-linked oxygen functional group at the 6-position. Chem. Pharm. Bull., 1998, 46(2), 287-293.
[254]
Okazaki, T.; Suga, A.; Watanabe, T.; Kikuchi, K.; Kurihara, H.; Shibasaki, M.; Fujimori, A.; Inagaki, O.; Yanagisawa, U. Studies on nonpeptide angiotensin II receptor antagonists. I. Synthesis and biological evaluation of pyrazolo[1,5-b] [1,2,4]triazole derivatives with alkyl substituents. Chem. Pharm. Bull., 1998, 46(1), 69-78.
[255]
Mertenskoetter, T.; Kaptur, P.E. Update on microbicide research and development-seeking new HIV prevention tools for women. Eur. J. Med. Res., 2011, 16(2), 1-6.
[256]
Doncel, G.; Mauck, C. Vaginal microbicides: a novel approach to preventing sexual transmission of HIV. Curr. HIV/AIDS Rep., 2004, 1(2), 25-32.
[257]
Turpin, J.A. Considerations and development of topical microbicides to inhibit the sexual transmission of HIV. Expert Opin. Invest. Drugs, 2002, 11(1), 1077-1097.
[258]
McFadden, K.; Fletcher, P.; Rossi, F. Kantharaju; Umashankara, M.; Pirrone, V.; Rajagopal, S.; Gopi, H.; Krebs, F.C.; Martin-Garcia, J.; Shattock, R.J.; Chaikena, I. Antiviral breadth and combination potential of peptide triazoleHIV-1 entry inhibitors. Antimicrob. Agents Chemother., 2012, 56(2), 1073-1080.
[259]
Cheng, H.; Wan, J.; Lin, M.I.; Liu, Y.; Lu, X.; Liu, J.; Xu, Y.; Chen, J.; Tu, Z.; Cheng, Y.S.; Ding, K. Design, synthesis, and in vitro biological evaluation of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents targeting virus nucleoprotein. J. Med. Chem., 2012, 55(5), 2144-2153.
[260]
Basaran, E.; Karakucuk-Iyidogan, A.; Schols, D.; Oruc-Emre, E.E. Synthesis of novel chiral sulfonamide-bearing 1,2,4-triazole-3-thione analogs derived from D- and L-phenylalanine esters as potential anti-influenza agents. Chirality, 2016, 28(6), 495-513.
[261]
Cao, X.; Wang, W.; Wang, S.; Bao, L. Asymmetric synthesis of novel triazole derivatives and them in vitro antiviral activity and mechanism of action. Eur. J. Med. Chem., 2017, 139(1), 718-725.
[262]
Youssif, B.G.; Mohamed, Y.A.; Salim, M.T.; Inagaki, F.; Mukai, C.; Abdu-Allah, H.H. Synthesis of some benzimidazole derivatives endowed with 1,2,3-triazole as potential inhibitors of hepatitis C virus. Acta Pharm., 2016, 66(2), 219-231.
[263]
He, Y.W.; Dong, C.Z.; Zhao, J.Y.; Ma, L.L.; Li, Y.H.; Aisa, H.A. 1,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses. Eur. J. Med. Chem., 2014, 76(1), 245-255.
[264]
Ferreira, S.B.; Sodero, A.C.; Cardoso, M.F.; Lima, E.S.; Kaiser, C.R.; Silva, F.P.; Ferreira, V.F. Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as α-glucosidases inhibitors. J. Med. Chem., 2010, 53(6), 2364-2375.
[265]
Xie, W.; Zhang, J.; Ma, X.; Yang, W.; Zhou, Y.; Tang, X.; Zou, Y.; Li, H.; He, J.; Xie, S.; Zhao, Y.; Liu, F. Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors. Chem. Biol. Drug Des., 2015, 86(5), 1087-1092.
[266]
Yu, F.; Jia, Y.L.; Wang, H.F.; Zheng, J.; Cui, Y.; Fang, X.Y.; Zhang, L.M.; Chen, Q.X. Synthesis of triazole schiff’s base derivatives and their inhibitory kinetics on tyrosinase activity. Plos One, 2015, 10(9)e0138578
[267]
Rafiq, M.; Saleem, M.; Hanif, M.; Kang, S.K.; Seo, S.Y.; Lee, K.H. Synthesis, structural elucidation and bioevaluation of 4-amino-1,2,4-triazole-3-thione’s Schiff base derivatives. Arch. Pharm. Res., 2016, 39(2), 161-171.
[268]
Hamann, A.R.; de Kock, C.; Smith, P.J.; van Otterlo, W.A.; Blackie, M.A. Synthesis of novel triazole-linked mefloquine derivatives: Biological evaluation against Plasmodium falciparum. Bioorg. Med. Chem. Lett., 2014, 24(23), 5466-5469.
[269]
Siddiqui, A.A.; Mishra, R.; Kumar, R.; Rashid, M.; Khaidem, S. Synthesis, spectral characterization, and pharmacological screening of some 4-[1-(aryl) methylidene-amino]-3-(4-pyridyl)-5-mercapto-4H-1,2,4-triazole derivatives. J. Pharm. Bioallied Sci., 2010, 2(2), 109-112.
[270]
Corrales, R.C.; de Souza, N.B.; Pinheiro, L.S.; Abramo, C.; Coimbra, E.S.; Da Silva, A.D. Thiopurine derivatives containing triazole and steroid: Synthesis, antimalarial and antileishmanial activities. Biomed. Pharmacother., 2011, 65(3), 198-203.
[271]
Sato, T.; Ashizawa, N.; Iwanaga, T.; Nakamura, H.; Matsumoto, K.; Inoue, T.; Nagata, O. Design, synthesis, and pharmacological and pharmacokinetic evaluation of 3-phenyl-5-pyridyl-1,2,4-triazole derivatives as xanthine oxidoreductase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(1), 184-187.
[272]
Naito, Y.; Akahoshi, F.; Takeda, S.; Okada, T.; Kajii, M.; Nishimura, H.; Sugiura, M.; Fukaya, C.; Kagitani, Y. Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia. J. Med. Chem., 1996, 39(15), 3019-3029.
[273]
Moulin, A.; Demange, L.; Ryan, J.; Mousseaux, D. Sanchez. P.; Berge, G.; Gagne, D.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J.C.; Fehrentz, J.A.; Martinez, J. New trisubstituted 1,2,4-triazole derivatives as potent ghrelin receptor antagonists. 3. Synthesis and pharmacological in vitro and in vivo evaluations. J. Med. Chem., 2008, 51(3), 689-693.
[274]
Akbarzadeh, T.; Tabatabai, S.A.; Khoshnoud, M.J.; Shafaghi, B.; Shafiee, A. Design and synthesis of 4H-3-(2-phenoxy)phenyl-1,2,4-triazole derivatives as benzodiazepine receptor agonists. Bioorg. Med. Chem., 2003, 11(5), 769-773.
[275]
Demange, L.; Boeglin, D.; Moulin, A.; Mousseaux, D.; Ryan, J.; Berge, G.; Gagne, D.; Heitz, A.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J.C.; Fehrentz, J.A.; Martinez, J. Synthesis and pharmacological in vitro and in vivo evaluations of novel triazole derivatives as ligands of the ghrelin receptor. 1. J. Med. Chem., 2007, 50(8), 1939-1957.
[276]
Bekircan, O.; Mentese, E.; Ulker, S.; Kucuk, C. Synthesis of some new 1,2,4-triazole derivatives starting from 3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol with anti-lipase and anti-urease activities. Arch. Pharm., 2014, 347(6), 387-397.
[277]
Gumrukcuoglu, N.; Sokmen, B.B.; Ugras, S.; Ugras, H.I.; Yanardag, R. Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new 1,4-butylene bridged bis-1,2,4-triazole derivatives. J. Enzyme Inhib. Med. Chem., 2013, 28(1), 89-94.
[278]
Das, A.; Adak, A.K.; Ponnapalli, K.; Lin, C.H.; Hsu, K.C.; Yang, J.M.; Hsu, T.A.; Lin, C.C. Design and synthesis of 1,2,3-triazole-containing N-acyl zanamivir analogs as potent neuraminidase inhibitors. Eur. J. Med. Chem., 2016, 123(2), 397-406.
[279]
Faidallah, H.M.; Panda, S.S.; Serrano, J.C.; Girgis, A.S.; Khan, K.A.; Alamry, K.A.; Therathanakorn, T.; Meyers, M.J.; Sverdrup, F.M.; Eickhoff, C.S.; Getchell, S.G.; Katritzky, A.R. Synthesis, antimalarial properties and 2D-QSAR studies of novel triazole-quinine conjugates. Bioorg. Med. Chem., 2016, 24(16), 3527-3539.
[280]
Gong, Z.; Peng, Y.; Qiu, J.; Cao, A.; Wang, G.; Peng, Z. Synthesis, In vitro α-glucosidase inhibitory activity and molecular docking studies of novel benzothiazole-triazole derivatives. Molecules, 2017, 22(9), 1555-1565.
[281]
Khan, I.; Tantray, M.A.; Hamid, H.; Alam, M.S.; Kalam, A.; Hussain, F.; Dhulap, A. Synthesis of pyrimidin-4-one-1,2,3-triazole conjugates as glycogen synthase kinase-3β inhibitors with anti-depressant activity. Bioorg. Chem., 2016, 68(1), 41-55.
[282]
Lebeau, A. Abrioux; C.; Benimelis, D.; Benfodda, Z.; Meffre, P. Synthesis of 1,4-disubstituted 1,2,3-triazole derivatives using click chemistry and their src kinase activities. Med. Chem., 2016, 13(1), 40-48.
[283]
Li, Y.S.; Tian, H.; Zhao, D.S.; Hu, D.K.; Liu, X.Y.; Jin, H.W.; Song, G.P.; Cui, Z.N. Synthesis and bioactivity of pyrazole and triazole derivatives as potential PDE4 inhibitors. Bioorg. Med. Chem. Lett., 2016, 26(15), 3632-3635.
[284]
Lu, K.; Cai, L.; Zhang, X.; Wu, G.; Xu, C.; Zhao, Y.; Gong, P. Design, synthesis, and biological evaluation of novel substituted benzamide derivatives bearing a 1,2,3-triazole moiety as potent human dihydroorotate dehydrogenase inhibitors. Bioorg. Chem., 2017, 76(1), 528-537.
[285]
Ouach, A.; Pin, F.; Bertrand, E.; Vercouillie, J.; Gulhan, Z.; Mothes, C.; Deloye, J.B.; Guilloteau, D.; Suzenet, F.; Chalon, S.; Routier, S. Design of α7 nicotinic acetylcholine receptor ligands using the (het)Aryl-1,2,3-triazole core: Synthesis, in vitro evaluation and SAR studies. Eur. J. Med. Chem., 2016, 107(1), 153-164.
[286]
Patil, S.R.; Asrondkar, A.; Patil, V.; Sangshetti, J.N. Kalam, Khan, F.A.; Damale, M.G.; Patil, R.H.; Bobade, A.S.; Shinde, D.B. Antileishmanial potential of fused 5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiols: Synthesis, biological evaluations and computational studies. Bioorg. Med. Chem. Lett., 2017, 27(16), 3845-3850.
[287]
Song, Z.; Liu, Y.; Dai, Z.; Liu, W.; Zhao, K.; Zhang, T.; Hu, Y.; Zhang, X.; Dai, Y. Synthesis and aromatase inhibitory evaluation of 4-N-nitrophenyl substituted amino-4H-1,2,4-triazole derivatives. Bioorg. Med. Chem., 2016, 24(19), 4723-4730.
[288]
Wang, B.L.; Zhang, L.Y.; Liu, X.H.; Ma, Y.; Zhang, Y.; Li, Z.M.; Zhang, X. Synthesis, biological activities and SAR studies of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases as ketol-acid reductoisomerase inhibitors. Bioorg. Med. Chem. Lett., 2017, 27(24), 5457-5462.
[289]
Wang, G.; Peng, Z.; Wang, J.; Li, J.; Li, X. Synthesis and biological evaluation of novel 2,4,5-triarylimidazole-1,2,3-triazole derivatives via click chemistry as α-glucosidase inhibitors. Bioorg. Med. Chem. Lett., 2016, 26(23), 5719-5723.
[290]
Wang, G.; Peng, Z.; Wang, J.; Li, X.; Li, J. Synthesis, in vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors. Eur. J. Med. Chem., 2017, 125(1), 423-429.
[291]
Wang, Y.; Sun, X.; Yang, D.; Guo, Z.; Fan, X.; Nie, M.; Zhang, F.; Liu, Y.; Li, Y.; Gong, P. Design, synthesis, and structure-activity relationship of novel and effective apixaban derivatives as FXa inhibitors containing 1,2,4-triazole/pyrrole derivatives as P2 binding element. Bioorg. Med. Chem., 2016, 24(21), 5646-5661.
[292]
Zhang, T.J.; Wu, Q.X.; Li, S.Y.; Wang, L.; Sun, Q.; Zhang, Y.; Meng, F.H.; Gao, H. Synthesis and evaluation of 1-phenyl-1H-1,2,3-triazole-4-carboxylic acid derivatives as xanthine oxidase inhibitors. Bioorg. Med. Chem. Lett., 2017, 27(16), 3812-3816.
[293]
Sahu, J.K.; Ganguly, S.; Kaushik, A. Triazoles: A valuable insight into recent developments and biological activities. Chin. J. Nat. Med., 2013, 11(5), 456-465.
[294]
Kumari, S.; Kumar, N.; Drabu, S.; Sharma, P.K. Advances in synthetic approach toand antifungal activity of triazoles. Beilstein J. Org. Chem., 2011, 7(1), 668-677.
[295]
Thakur, A.; Gupta, P.S.; Shukla, P.K.; Verma, A.; Pathak, P. 1,2,4-Triazole scafolds: Recent advances and pharmacologicalapplications. Int. J. Curr. Res. Acad. Rev., 2016, 4(2), 277-296.
[296]
Kong, Z.; Li, M.; An, J.; Chen, J.; Bao, Y.; Francis, F.; Dai, X. The fungicide triadimefon affects beer flavor and composition by influencing Saccharomyce scerevisiae metabolism. Sci. Rep., 2016, 6(1), 33552.
[297]
Abdelhady, D.H.; El-Magd, M.A.; Elbialy, Z.I.; Saleh, A.A. Bromuconazole-induced hepatotoxicity isaccompanied by upregulation of PXR/CYP3A1 anddownregulation of CAR/CYP2B1 gene expression. Toxicol. Mech. Meth, 2017.
[http://dx.doi.org/10.1080/15376516.2017. 1333555. ]
[298]
Zervos, M.; Meunier, F. Fluconazole (Diflucan®): A review. Int. J. Antimicrob. Agents, 1993, 3(1), 147-170.
[299]
Henry, M.J. Mode of action of the fungicide Flusilazole in ustilago maydis. Pestic. Sci., 1990, 28, 35-42.
[300]
Zhang, H.Z.; Damu, G.L.V.; Cai, G.X.; Zhou, C.H. Current developments in the syntheses of 1,2,4-triazole compounds. Curr. Org. Chem., 2014, 18(1), 359-406.
[301]
Farowski, F.; Vehreschild, J.J.; Cornely, O.A. Posaconazole: A next-generation triazole antifungal. Future Microbiol., 2007, 2(3), 231-243.
[302]
Bailey, E.M.; Krakovsky, D.J.; Rybak, M.J. The triazole antifungal agents: A review of itraconazole and fluconazole. Pharmacotherapy, 1990, 10(2), 146-153.
[303]
Koike, M.; Norikura, R.; Iwatani, K.; Sugeno, K.; Takahashi, S.; Nakagawa, Y. Structure determination of metabolites ofrilmazafone, a lW-1,2,4-triazolyl benzophenonederivative in monkey urine. Xenobiotica, 1988, 18(3), 257-268.
[304]
Cyr, M.; Brown, C.S. Nefazodone: Its place among antidepressants. Ann. Pharmacother., 1996, 30(1), 1006-1012.
[305]
Chohan, Z.H.; Hanif, M. Antibacterial and antifungal metal based triazole Schiff bases. J. Enzyme Inhib. Med. Chem., 2013, 28(5), 944-953.
[306]
El-Ella, D.A.A.; Hussein, M.M.; Serya, R.A.T.; Naby, R.M.A.; Al-Abd, A.M.; Saleh, D.O.; El-Eraky, W.I.; Abouzid, K.A.M. Molecular design and synthesis of 1,4-disubstituted piperazinesas α1-adrenergic receptor blockers. Bioorg. Chem., 2014, 54(1), 21-30.
[307]
Wheless, J.W.; Vazquez, B. Rufinamide: A novel broad-spectrum antiepileptic drug. Epilepsy Curr., 2010, 10(1), 1-6.
[308]
Elgemeie, G.H.; Abu-Zaied, M.A.; Nawwar, G.A. First novel synthesis of triazolethioglycosides as ribavirin analogues. Nucleosides Nucleotides Nucleic Acids, 2018, 37(2), 112-123.
[309]
Arshad, M. An insight to the synthetically obtained triazole possessing numerous biological activities. Int. J. Pharm. Pharm. Sci., 2014, 6(9), 16-23.
[310]
Varughese, S.; Azim, Y.; Desiraju, G.R. Molecular complexes of alprazolam with carboxylic acids, boric acid, boronic acids, and phenols. Evaluation of supramolecular heterosynthons mediated by a triazole ring. J. Pharm. Sci., 2010, 99(9), 3743-3753.
[311]
Haynes, B.P.; Dowsett, M.; Miller, W.R.; Dixon, J.M.; Bhatnagar, A.S. The pharmacology of letrozole. J. Steroid Biochem. Mol. Biol., 2003, 87(1), 35-45.
[312]
El Rayes, S.M. Convenient synthesis and antimicrobial activity of some novel amino acid coupled triazoles. Molecules, 2010, 15(1), 6759-6772.
[313]
Fichtali, I.; Chraibi, M.; El Aroussi, F.; Ben-Tama, A.; El Hadrami, E.M.; Benbrahim, K.F.; Stiriba, S.E. Synthesis of some 1,2,3-triazoles derivatives and evaluation of their antimicrobial activity. Der. Pharma. Chemica., 2016, 8(5), 236-242.
[314]
Sultana, N.; Arayne, M.S. In vitro activity of cefadroxil, cephalexin, cefatrizine and cefpirome in presence of essential and trace elements. Pak. J. Pharm. Sci., 2007, 20(4), 305-310.
[315]
Sarma, P.S.; Rao, C.N.; Surayanarayana, M.V.; Reddy, P.P.; Khalilluah, M.; Praveen, C. Synthesis and characterization of potentialimpurities of the antimigraine drug, rizatriptan benzoate. Synth. Commun., 2008, 38(1), 603-612.
[316]
Zhang, C.L.; Heinemann, U. Effects of the triazole derivative loreclezole (R72063) on stimulus induced ionic and field potential responses and on different patterns of epileptiform activity induced by low magnesium in rat entorhinal cortex-hippocampal slices. Naunyn Schmiedebergs Arch. Pharmacol., 1992, 346(1), 581-587.