Generic placeholder image

Current Pharmaceutical Design

Author(s): Shikha Sharma*, Nitin Mittal and Bimal Krishna Banik

DOI: 10.2174/0113816128271288231023045049

DownloadDownload PDF Flyer Cite As
Chemistry and Therapeutic Aspect of Triazole: Insight into the Structure-activity Relationship

Page: [2702 - 2720] Pages: 19

  • * (Excluding Mailing and Handling)

Abstract

The triazole ring is a highly significant heterocycle that occurs naturally in many commodities and is a common feature in pharmaceuticals. Recently, heterocyclic compounds and their derivatives have been getting a lot of attention in medicinal chemistry because they have a lot of pharmacological and biological potential. For example, a lot of drugs have nitrogen-containing heterocyclic moieties. The triazole ring is often used as a bio-isostere of the oxadiazole nucleus. The oxygen atom in the oxadiazole nucleus is replaced by nitrogen in the triazole analogue. This article explores the pharmacological properties of the triazole moiety, including but not limited to antibacterial, analgesic, anticonvulsant, anthelmintic, anti-inflammatory, antitubercular, antimalarial, antioxidant, antiviral, and other properties. Additionally, we discuss the diverse multi- target pharmacological activities exhibited by triazole-based compounds. Based on a literature review, it is evident that triazole-based chemicals hold significant potential for various applications.

[1]
Pagniez F, Lebouvier N, Na YM, et al. Biological exploration of a novel 1,2,4-triazole-indole hybrid molecule as antifungal agent. J Enzyme Inhib Med Chem 2020; 35(1): 398-403.
[http://dx.doi.org/10.1080/14756366.2019.1705292] [PMID: 31899979]
[2]
Bozorov K, Zhao J, Aisa HA. 1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview. Bioorg Med Chem 2019; 27(16): 3511-31.
[http://dx.doi.org/10.1016/j.bmc.2019.07.005] [PMID: 31300317]
[3]
Palkó M, El Haimer M, Kormányos Z, Fülöp F. Synthesis of novel N-heterocyclic compounds containing 1,2,3-Triazole ring system via domino, “click” and RDA reactions. Molecules 2019; 24(4): 772-83.
[http://dx.doi.org/10.3390/molecules24040772] [PMID: 30795610]
[4]
Potts KT. The chemistry of 1,2,4-triazoles. Chem Rev 1961; 61(2): 87-127.
[http://dx.doi.org/10.1021/cr60210a001]
[5]
Ulloora S, Shabaraya R, Adhikari AV. Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies. Bioorg Med Chem Lett 2013; 23(11): 3368-72.
[http://dx.doi.org/10.1016/j.bmcl.2013.03.086] [PMID: 23623419]
[6]
Kadaba PK. Triazolines. 14. 1,2,3-Triazolines and triazoles. A new class of anticonvulsants. Drug design and structure-activity relationships. J Med Chem 1988; 31(1): 196-203.
[http://dx.doi.org/10.1021/jm00396a032] [PMID: 3336019]
[7]
Guan LP, Jin QH, Tian GR, Chai KY, Quan ZS. 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): 254-62.
[PMID: 17727789]
[8]
Padmavathi V, Sudhakar Reddy G, Padmaja A, Kondaiah P. Ali-Shazia. Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. Eur J Med Chem 2009; 44(5): 2106-12.
[http://dx.doi.org/10.1016/j.ejmech.2008.10.012] [PMID: 19036476]
[9]
Zoumpoulakis P, Camoutsis C, Pairas G, et al. Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorg Med Chem 2012; 20(4): 1569-83.
[http://dx.doi.org/10.1016/j.bmc.2011.12.031] [PMID: 22264752]
[10]
De La Rosa M, Kim HW, Gunic E, et al. Tri-substituted triazoles as potent non-nucleoside inhibitors of the HIV-1 reverse transcriptase. Bioorg Med Chem Lett 2006; 16(17): 4444-9.
[http://dx.doi.org/10.1016/j.bmcl.2006.06.048] [PMID: 16806925]
[11]
Dong WL, Liu ZX, Liu XH, Li ZM, Zhao WG. Synthesis and antiviral activity of new acrylamide derivatives containing 1,2,3-thiadiazole as inhibitors of hepatitis B virus replication. Eur J Med Chem 2010; 45(5): 1919-26.
[http://dx.doi.org/10.1016/j.ejmech.2010.01.032] [PMID: 20149495]
[12]
Boechat N, Ferreira VF, Ferreira SB, Lourdes GF. Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives. J Med Chem 2011; 54(17): 5988-99.
[http://dx.doi.org/10.1021/jm2003624] [PMID: 21776985]
[13]
Labanauskas L, Udrenaite E, Gaidelis P, Brukštus 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): 255-9.
[http://dx.doi.org/10.1016/j.farmac.2003.11.002] [PMID: 15081342]
[14]
Wang G, Peng Z, Wang J, Li X, Li J. Triazole analogues as potential pharmacological agents: A brief review. Eur J Med Chem 2017; 125: 423-9.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.067] [PMID: 27689725]
[15]
Al-Soud YA, Al-Dweri MN, Al-Masoudi NA. Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivatives. Farmaco 2004; 59(10): 775-83.
[http://dx.doi.org/10.1016/j.farmac.2004.05.006] [PMID: 15474054]
[16]
Mathew V, Keshavayya J, Vaidya VP, Giles D. Studies on synthesis and pharmacological activities of 3,6-disubstituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and their dihydro analogues. Eur J Med Chem 2007; 42(6): 823-40.
[http://dx.doi.org/10.1016/j.ejmech.2006.12.010] [PMID: 17331622]
[17]
Shaikh MH, Subhedar DD, Arkile M, et al. Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent. Bioorg Med Chem Lett 2016; 26(2): 561-9.
[http://dx.doi.org/10.1016/j.bmcl.2015.11.071] [PMID: 26642768]
[18]
Khan I, Ali S, Hameed S, et al. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Eur J Med Chem 2010; 45(11): 5200-7.
[http://dx.doi.org/10.1016/j.ejmech.2010.08.034] [PMID: 20828889]
[19]
Manohar S, Khan SI, Rawat DS. Synthesis of 4-aminoquinoline-1,2,3-triazole and 4-aminoquinoline-1,2,3-triazole-1,3,5-triazine hybrids as potential antimalarial agents. Chem Biol Drug Des 2011; 78(1): 124-36.
[http://dx.doi.org/10.1111/j.1747-0285.2011.01115.x] [PMID: 21457474]
[20]
Chu XM, Wang C, Wang WL, et al. Triazole derivatives and their antiplasmodial and antimalarial activities. Eur J Med Chem 2019; 166: 206-23.
[http://dx.doi.org/10.1016/j.ejmech.2019.01.047] [PMID: 30711831]
[21]
Yang L, Wu Y, Yang Y, Wen C, Wan JP. Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide. Beilstein J Org Chem 2018; 14: 2348-53.
[http://dx.doi.org/10.3762/bjoc.14.210] [PMID: 30254699]
[22]
Girmenia C. New generation azole antifungals in clinical investigation. Expert Opin Investig Drugs 2009; 18(9): 1279-95.
[http://dx.doi.org/10.1517/13543780903176407] [PMID: 19678798]
[23]
Smith J, Safdar N, Knasinski V, et al. Voriconazole therapeutic drug monitoring. Antimicrob Agents Chemother 2006; 50(4): 1570-2.
[24]
Giordano SH, Valero V, Buzdar AU, Hortobagyi GN. Male breast carcinoma: Increased awareness needed. Am J Clin Oncol 2002; 25(3): 235-7.
[http://dx.doi.org/10.1097/00000421-200206000-00006] [PMID: 12040279]
[25]
Wingrove PB, Wafford KA, Bain C, Whiting PJ. The modulatory action of loreclezole at the gamma-aminobutyric acid type A receptor is determined by a single amino acid in the beta 2 and beta 3 subunit. Proc Natl Acad Sci USA 1994; 91(10): 4569-73.
[http://dx.doi.org/10.1073/pnas.91.10.4569] [PMID: 8183949]
[26]
Millson DS, Tepper SJ, Rapoport AM. Migraine pharmacotherapy with oral triptans: A rational approach to clinical management. Expert Opin Pharmacother 2000; 1(3): 391-404.
[http://dx.doi.org/10.1517/14656566.1.3.391] [PMID: 11249525]
[27]
Goss PE. Pre-clinical and clinical review of vorozole, a new third generation aromatase inhibitor. Breast Cancer Res Treat 1998; 49(S1) (Suppl. 1): S59-65.
[http://dx.doi.org/10.1023/A:1006052923468] [PMID: 9797019]
[28]
Crotty S, Cameron C, Andino R. Ribavirin’s antiviral mechanism of action: Lethal mutagenesis? J Mol Med 2002; 80(2): 86-95.
[http://dx.doi.org/10.1007/s00109-001-0308-0] [PMID: 11907645]
[29]
Alvarez D, Dieterich DT, Brau N, Moorehead L, Ball L, Sulkowski MS. Zidovudine use but not weight-based ribavirin dosing impacts anaemia during HCV treatment in HIV-infected persons. J Viral Hepat 2006; 13(10): 683-9.
[http://dx.doi.org/10.1111/j.1365-2893.2006.00749.x] [PMID: 16970600]
[30]
Miura M, Otani K, Ohkubo T. Identification of human cytochrome P450 enzymes involved in the formation of 4-hydroxyestazolam from estazolam. Xenobiotica 2005; 35(5): 455-65.
[http://dx.doi.org/10.1080/00498250500111612] [PMID: 16012077]
[31]
Borras L, Timary P, Constant E-L, Huguelet P, Eytan A. Successful treatment of alcohol withdrawal with trazodone. Pharmacopsychiatry 2006; 39(6): 232.
[http://dx.doi.org/10.1055/s-2006-951385] [PMID: 17124647]
[32]
Béchir M, Schwegler K, Chenevard R, et al. Anxiolytic therapy with alprazolam increases muscle sympathetic activity in patients with panic disorders. Auton Neurosci 2007; 134(1-2): 69-73.
[http://dx.doi.org/10.1016/j.autneu.2007.01.007] [PMID: 17363337]
[33]
Wolf BC, Lavezzi WA, Sullivan LM, Middleberg RA, Flannagan LM. Alprazolam-related deaths in Palm Beach County. Am J Forensic Med Pathol 2005; 26(1): 24-7.
[34]
Önkol T. Doğruer DS, Uzun L, Adak S, Özkan S, Fethi Şahin M. Synthesis and antimicrobial activity of new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. J Enzyme Inhib Med Chem 2008; 23(2): 277-84.
[http://dx.doi.org/10.1080/14756360701408697] [PMID: 18343916]
[35]
Rezki N, Al-Yahyawi AM, Bardaweel SK, Al-Blewi FF. Synthesis of novel 2,5-disubstituted-1,3,4-thiadiazoles clubbed 1,2,4-triazole, 1,3,4-thiadiazole, 1,3,4-oxadiazole and/or schiff base as potential antimicrobial and antiproliferative agents. Molecules 2015; 20(9): 16048-67.
[http://dx.doi.org/10.3390/molecules200916048]
[36]
Yang L, Ge S, Huang J, Bao X. Synthesis of novel (E)-2-(4-(1H-1,2,4-triazol-1-yl)styryl)-4-(alkyl/arylmethyleneoxy)quinazoline derivatives as antimicrobial agents. Mol Divers 2018; 22(1): 71-82.
[http://dx.doi.org/10.1007/s11030-017-9792-1] [PMID: 29119421]
[37]
Ni T, Pang L, Cai Z, et al. Design, synthesis, and in vitro antifungal evaluation of novel triazole derivatives bearing alkynyl side chains. J Saudi Chem Soc 2019; 23(5): 576-85.
[http://dx.doi.org/10.1016/j.jscs.2018.10.003]
[38]
Tang KW, Yang SC, Tseng CH. Design, synthesis, and anti-bacterial evaluation of triazolyl-pterostilbene derivatives. Int J Mol Sci 2019; 20(18): 4564-81.
[http://dx.doi.org/10.3390/ijms20184564] [PMID: 31540106]
[39]
Lipeeva AV, Zakharov DO, Burova LG, et al. Design, synthesis and antibacterial activity of coumarin-1,2,3-triazole hybrids obtained from natural furocoumarin peucedanin. Molecules 2019; 24(11): 2126-49.
[http://dx.doi.org/10.3390/molecules24112126] [PMID: 31195697]
[40]
Han X, Wang S, Zhang N, et al. Novel triazole derivatives containing different ester skeleton: Design, synthesis, biological evaluation and molecular docking. Chem Pharm Bull 2020; 68(1): 64-9.
[http://dx.doi.org/10.1248/cpb.c19-00624] [PMID: 31708557]
[41]
Addo JK, Owusu-Ansah E, Dayie NTKD, Cheseto X, Torto B. Synthesis of 1,2,3-triazole-thymol derivatives as potential antimicrobial agents. Heliyon 2022; 8(10)
[http://dx.doi.org/10.2139/ssrn.4144500]
[42]
Aziz Ali A, Gogoi D, Chaliha AK, et al. Synthesis and biological evaluation of novel 1,2,3-triazole derivatives as anti-tubercular agents. Bioorg Med Chem Lett 2017; 27(16): 3698-703.
[http://dx.doi.org/10.1016/j.bmcl.2017.07.008] [PMID: 28712709]
[43]
Patel VM, Patel NB, Chan-Bacab MJ, Rivera G. Synthesis, biological evaluation and molecular dynamics studies of 1,2,4-triazole clubbed Mannich bases. Comput Biol Chem 2018; 76: 264-74.
[44]
Ramprasad J, Kumar Sthalam V, Linga Murthy Thampunuri R, et al. Synthesis and evaluation of a novel quinoline-triazole analogs for antitubercular properties via molecular hybridization approach. Bioorg Med Chem Lett 2019; 29(20): 126671.
[http://dx.doi.org/10.1016/j.bmcl.2019.126671] [PMID: 31526604]
[45]
Shiva Raju K. AnkiReddy S, Sabitha G, et al. Synthesis and biological evaluation of 1H-pyrrolo[2,3-d]pyrimidine-1,2,3-triazole derivatives as novel anti-tubercular agents. Bioorg Med Chem Lett 2019; 29(2): 284-90.
[http://dx.doi.org/10.1016/j.bmcl.2018.11.036] [PMID: 30497913]
[46]
Satyendra RV, Vishnumurthy KA, Vagdevi HM, Rajesh KP, Manjunatha H, Shruthi A. Synthesis, in vitro antioxidant, anthelmintic and molecular docking studies of novel dichloro substituted benzoxazole-triazolo-thione derivatives. Eur J Med Chem 2011; 46(7): 3078-84.
[47]
Paprocka R. Kołodziej P, Wiese-Szadkowska M, Helmin-Basa A, Bogucka-Kocka A. Evaluation of anthelmintic and anti-inflammatory activity of 1,2,4-triazole derivatives. Molecules 2022; 27(14): 4488.
[http://dx.doi.org/10.3390/molecules27144488]
[48]
Mahdavi M, Akbarzadeh T, Sheibani V, et al. Synthesis of two novel 3-Amino-5-[4-chloro-2-phenoxyphenyl]-4H-1,2,4-triazoles with anticonvulsant activity. Iran J Pharm Res 2010; 9(3): 265-9.
[PMID: 24363736]
[49]
Siddiqui N, Ahsan W. Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening. Eur J Med Chem 2010; 45(4): 1536-43.
[http://dx.doi.org/10.1016/j.ejmech.2009.12.062] [PMID: 20116140]
[50]
Zheng Y, Wang SB, Cao X, Liu DC, Shu B, Quan ZS. Design, synthesis and anticonvulsant activity evaluation of novel 4-(4-substitutedphenyl)-3-methyl-1H-1,2,4-triazol-5(4H)-ones. Drug Res 2013; 64(1): 40-6.
[http://dx.doi.org/10.1055/s-0033-1351316] [PMID: 23965799]
[51]
Zhang HJ, Shen QK, Jin CM, Quan ZS. Synthesis and pharmacological evaluation of new 3,4-dihydroisoquinolin derivatives containing heterocycle as potential anticonvulsant agents. Molecules 2016; 21(12): 1635-52.
[http://dx.doi.org/10.3390/molecules21121635] [PMID: 27916842]
[52]
Dehestani L, Ahangar N, Hashemi SM, et al. Design, synthesis, in vivo and in silico evaluation of phenacyl triazole hydrazones as new anticonvulsant agents. Bioorg Chem 2018; 78: 119-29.
[http://dx.doi.org/10.1016/j.bioorg.2018.03.001] [PMID: 29550532]
[53]
Song MX, Wang ZY, He SH, et al. Synthesis and evaluation of the anticonvulsant activities of 4-(2-(Alkylthio)benzo[d]oxazol-5-yl)-2,4-dihydro-3H-1,2,4-triazol-3-ones. Molecules 2018; 23(4): 756-68.
[http://dx.doi.org/10.3390/molecules23040756] [PMID: 29587394]
[54]
Verma KK, Singh UK, Jain J. Design, synthesis and biological activity of some 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives. Cent Nerv Syst Agents Med Chem 2019; 19: 197-205.
[http://dx.doi.org/10.2174/1871524919666190722144424]
[55]
Wang S, Liu H, Wang X, et al. Synthesis and evaluation of anticonvulsant activities of 7‐phenyl‐4,5,6,7‐tetrahydrothieno[3,2‐b]pyridine derivatives. Arch Pharm 2019; 352(10): 1900106.
[http://dx.doi.org/10.1002/ardp.201900106] [PMID: 31364202]
[56]
Tozkoparan B, Küpeli E. Yeşilada E, Ertan M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory–analgesic activity. Bioorg Med Chem 2007; 15(4): 1808-14.
[http://dx.doi.org/10.1016/j.bmc.2006.11.029] [PMID: 17166724]
[57]
Almasirad A, Shafiee A, Abdollahi M, et al. Synthesis and analgesic activity of new 1,3,4-oxadiazoles and 1,2,4-triazoles. Med Chem Res 2011; 20(4): 435-42.
[http://dx.doi.org/10.1007/s00044-010-9335-0]
[58]
Shafi S, Mahboob Alam M, Mulakayala N, et al. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their anti-inflammatory and anti-nociceptive activities. Eur J Med Chem 2012; 49: 324-33.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.032] [PMID: 22305614]
[59]
Haider S, Alam MS, Hamid H, et al. Synthesis of novel 1,2,3-triazole based benzoxazolinones: Their TNF-α based molecular docking with in-vivo anti-inflammatory, antinociceptive activities and ulcerogenic risk evaluation. Eur J Med Chem 2013; 70: 579-88.
[http://dx.doi.org/10.1016/j.ejmech.2013.10.032] [PMID: 24211633]
[60]
Sarigol D, Uzgoren-Baran A, Tel BC, et al. Novel thiazolo[3,2-b]-1,2,4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies. Bioorg Med Chem 2015; 23(10): 2518-28.
[http://dx.doi.org/10.1016/j.bmc.2015.03.049] [PMID: 25868745]
[61]
Zhang HJ, Wang XZ, Cao Q, Gong GH, Quan ZS. Design, synthesis, anti-inflammatory activity, and molecular docking studies of perimidine derivatives containing triazole. Bioorg Med Chem Lett 2017; 27(18): 4409-14.
[http://dx.doi.org/10.1016/j.bmcl.2017.08.014] [PMID: 28823493]
[62]
Khan SA, Imam SM, Ahmad A, Basha SH, Husain A. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1, 3, 4-thiadiazole derivatives. J Saudi Chem Soc 2018; 22(4): 469-84.
[http://dx.doi.org/10.1016/j.jscs.2017.05.006]
[63]
Andrew N. Click chemistry synthesis, biological evaluation and docking study of some novel 2′-hydroxychalcone-triazole hybrids as potent anti-inflammatory agents. Bioorg Chem 2019.
[http://dx.doi.org/10.1016/j.bioorg.2019.103505]
[64]
Duan YC, Ma YC, Zhang E, Shi XJ, Wang MM, Ye XW. Design and synthesis of novel 1,2,3-triazole-dithiocarbamate hybrids as potential anticancer agent. Eur J Med Chem 2013; 62: 11-9.
[65]
Ma LY, Pang LP, Wang B, et al. Design and synthesis of novel 1,2,3-triazole-pyrimidine hybrids as potential anticancer agents. Eur J Med Chem 2014; 86: 368-80.
[http://dx.doi.org/10.1016/j.ejmech.2014.08.010] [PMID: 25180925]
[66]
Ashwini N, Garg M, Mohan CD, et al. Tocotrienol oxazine derivative antagonizes mammary tumor cell compensatory response to CoCl2-induced hypoxia. Bioorg Med Chem 2015; 23(18): 6157-65.
[http://dx.doi.org/10.1016/j.bmc.2015.07.069] [PMID: 26299825]
[67]
Al-Wahaibi LH, Abu-Melha HM. Synthesis of novel 1,2,4-triazolyl coumarin derivatives as potential anticancer agents. J Chem 2018; 5201374: 1-8.
[68]
Mahanti S, Sunkara S, Bhavani R. Synthesis, biological evaluation and computational studies of fused acridine containing 1,2,4-triazole derivatives as anticancer agents. Synth Commun 2019; 49(13): 1729-40.
[http://dx.doi.org/10.1080/00397911.2019.1608450]
[69]
Dhawan S, Awolade P, Kisten P, et al. Synthesis, cytotoxicity and antimicrobial evaluation of new coumarin-tagged β-lactam triazole hybrid. Chem Biodivers 2020; 17(1): e1900462.
[http://dx.doi.org/10.1002/cbdv.201900462] [PMID: 31788939]
[70]
Emami L, Sadeghian S, Mojaddami A, et al. Design, synthesis and evaluation of novel 1,2,4-triazole derivatives as promising anticancer agents. BMC Chem 2022; 16(1): 91.
[http://dx.doi.org/10.1186/s13065-022-00887-x] [PMID: 36369166]
[71]
Chinthala Y, Thakur S, Tirunagari S, et al. Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity. Eur J Med Chem 2015; 93: 564-73.
[72]
Avula SK, Khan A, Rehman NU, et al. Synthesis of 1H-1,2,3-triazole derivatives as new α-glucosidase inhibitors and their molecular docking studies. Bioorg Chem 2018; 81: 98-106.
[http://dx.doi.org/10.1016/j.bioorg.2018.08.008] [PMID: 30118991]
[73]
Saeedi M, Mohammadi-Khanaposhtani M, Pourrabia P, et al. Design and synthesis of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids as new anti-diabetic agents: In vitro α-glucosidase inhibition, kinetic and docking studies. Bioorg Chem 2019; 83: 161-9.
[74]
Küçükgüzel İ Tatar E, Küçükgüzel ŞG, Rollas S, De Clercq E. Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2,4-dihydro-3H-1,2,4-triazole-3- thiones and evaluation as antiviral/anti-HIV and anti-tuberculosis agents. Eur J Med Chem 2008; 43(2): 381-92.
[http://dx.doi.org/10.1016/j.ejmech.2007.04.010] [PMID: 17583388]
[75]
Jordao AK, Afonso PP, Ferreira VF, et al. Antiviral evaluation of N-amino-1,2,3-triazoles against Cantagalo virus replication in cell culture. Eur J Med Chem 2009; 44(9): 3777-83.
[76]
Mohammed I, Kummetha IR, Singh G, et al. 1,2,3-Triazoles as amide bioisosteres: Discovery of a new class of potent HIV-1 Vif antagonists. J Med Chem 2016; 59(16): 7677-82.
[http://dx.doi.org/10.1021/acs.jmedchem.6b00247] [PMID: 27509004]
[77]
Cao X, Wang W, Wang S, Bao L. Asymmetric synthesis of novel triazole derivatives and their in vitro antiviral activity and mechanism of action. Eur J Med Chem 2017; 139: 718-25.
[http://dx.doi.org/10.1016/j.ejmech.2017.08.057] [PMID: 28858766]