Generic placeholder image

Letters in Organic Chemistry

Author(s): Moustafa A. Gouda*, Ameen Ali Abu-Hashem*, Hoda Abdel Raouf Hussein and Ahmed S. Aly

DOI: 10.2174/1570178617666200417121205

DownloadDownload PDF Flyer Cite As
Recent Development in the Chemistry of Bicyclic 6+5 Systems, Part II: Chemistry of Triazolopyrimidine Derivatives

Page: [897 - 925] Pages: 29

  • * (Excluding Mailing and Handling)

Abstract

This review describes the synthesis and reactions of substituted triazolopyrimidines as building blocks toward polyfunctionalized heterocyclic compounds with pharmacological interest.

Keywords: 1, 2, 3-Triazolopyrimidines, 1, 2, 4-triazolopyrimidines, 3-amino-1, 2, 4-triazoles, 5-amino-1H-1, 2, 3-triazole-4- carboxamides, reactions, synthesis.

Graphical Abstract

[1]
El-Gendy, M.M.A.; Shaaban, M.; Shaaban, K.A.; El-Bondkly, A.M.; Laatsch, H. J. Antibiot. (Tokyo), 2008, 61(3), 149-157.
[http://dx.doi.org/10.1038/ja.2008.124] [PMID: 18503193]
[2]
Doláková, P.; Dracínský, M.; Masojídková, M.; Solínová, V.; Kašička, V.; Holý, A. Eur. J. Med. Chem., 2009, 44(6), 2408-2424.
[http://dx.doi.org/10.1016/j.ejmech.2008.09.031] [PMID: 18992968]
[3]
Abu-Hashem, A.A.; Hussein, H.A.R.; Abu-zied, K.M. Med. Chem. Res., 2017, 26, 120-130.
[http://dx.doi.org/10.1007/s00044-016-1733-5]
[4]
Abdelghani, E.; Said, S.A.; Assy, M.G.; Abdel Hamid, A.M.J. Iran. Chem. Soc., 2015, 12, 1809-1817.
[http://dx.doi.org/10.1007/s13738-015-0656-2]
[5]
El-Sayed, W.A.; Ali, O.M.; Faheem, M.S.; Zied, I.F.; Abdel-Rahman, A.A-H. J. Heterocycl. Chem., 2012, 49, 607-612.
[http://dx.doi.org/10.1002/jhet.832]
[6]
‏Said, S.A.; Amr, A.E.-G.E.; Sabry, N.M.; Abdalla, M.M. Eur. J. Med. Chem., 2009, 44, 4787-4792.
[7]
Nettekoven, M.; Adam, J-M.; Bendels, S.; Bissantz, C.; Fingerle, J.; Grether, U.; Grüner, S.; Guba, W.; Kimbara, A.; Ottaviani, G.; Püllmann, B.; Rogers-Evans, M.; Röver, S.; Rothenhäusler, B.; Schmitt, S.; Schuler, F.; Schulz-Gasch, T.; Ullmer, C. ChemMedChem, 2016, 11(2), 179-189.
[http://dx.doi.org/10.1002/cmdc.201500218] [PMID: 26228928]
[8]
Beyer, C.F.; Zhang, N.; Hernandez, R.; Vitale, D.; Lucas, J.; Nguyen, T.; Discafani, C.; Ayral-Kaloustian, S.; Gibbons, J. J. Cancer Res., 2008, 68, 2292-2300.
[http://dx.doi.org/10.1158/0008-5472.CAN-07-1420]
[9]
Li, H.; Tatlock, J.; Linton, A.; Gonzalez, J.; Jewell, T.; Patel, L.; Ludlum, S.; Drowns, M.; Rahavendran, S.V.; Skor, H.; Hunter, R.; Shi, S.T.; Herlihy, K.J.; Parge, H.; Hickey, M.; Yu, X.; Chau, F.; Nonomiya, J.; Lewis, C. J. Med. Chem., 2009, 52(5), 1255-1258.
[http://dx.doi.org/10.1021/jm8014537] [PMID: 19209845]
[10]
Caballero, A.B.; Marín, C.; Ramírez-Macías, I.; Rodríguez-Diéguez, A.; Quirós, M.; Salas, J.M.; Sánchez-Moreno, M. Polyhedron, 2012, 33, 137-144.
[http://dx.doi.org/10.1016/j.poly.2011.11.020]
[11]
Nasr, M.N.; Gineinah, M.M. Arch. Pharm. (Weinheim), 2002, 335(6), 289-295.
[http://dx.doi.org/10.1002/1521-4184(200208)335:6<289:AID-ARDP289>3.0.CO;2-Z] [PMID: 12210772]
[12]
Lipunova, G.N.; Nosova, E.V.; Kodess, M.I.; Charushin, V.N.; Rozin, Y.A.; Chasovskikh, O.M. Russ. J. Org. Chem., 2001, 37, 570-576.
[http://dx.doi.org/10.1023/A:1012498322793]
[13]
Hassaneen, H.M.; Abdallah, T.A.; Abdelhadi, H.A.; Hassaneen, H.M.E.; Pagni, R.M. Heteroatom Chem., 2003, 14, 491-497.
[http://dx.doi.org/10.1002/hc.10166]
[14]
Al-Zaydi, K.M.; Borik, R.M.; Elnagdi, M.H. Molecules, 2003, 8, 910-923.
[http://dx.doi.org/10.3390/81200910]
[15]
Isoda, S. Chem. Pharm. Bull. , 1991, 39, 1099-1105.
[16]
Gouda, M.A.; Berghot, M.A.; Abd El-Ghani, G.E.; Khalil, A.M. Lett. Org. Chem., 2020, 17, 2-23.
[http://dx.doi.org/10.2174/1570178616666190411102031]
[17]
Patil, V.; Kale, M.; Raichurkar, A.; Bhaskar, B.; Prahlad, D.; Balganesh, M.; Nandan, S.; Shahul Hameed, P. Bioorg. Med. Chem. Lett., 2014, 24(9), 2222-2225.
[http://dx.doi.org/10.1016/j.bmcl.2014.02.054] [PMID: 24703230]
[18]
Boechat, N.; Pinheiro, L.C.S.; Silva, T.S.; Aguiar, A.C.C.; Carvalho, A.S.; Bastos, M.M.; Costa, C.C.P.; Pinheiro, S.; Pinto, A.C.; Mendonça, J.S.; Dutra, K.D.B.; Valverde, A.L.; Santos-Filho, O.A.; Ceravolo, I.P.; Krettli, A.U. Molecules, 2012, 17(7), 8285-8302.
[http://dx.doi.org/10.3390/molecules17078285] [PMID: 22781441]
[19]
Kumar, J.; Meena, P.; Singh, A.; Jameel, E.; Maqbool, M.; Mobashir, M.; Shandilya, A.; Tiwari, M.; Hoda, N.; Jayaram, B. Eur. J. Med. Chem., 2016, 119, 260-277.
[http://dx.doi.org/10.1016/j.ejmech.2016.04.053] [PMID: 27227482]
[20]
Jameel, E.; Meena, P.; Maqbool, M.; Kumar, J.; Ahmed, W.; Mumtazuddin, S.; Tiwari, M.; Hoda, N.; Jayaram, B.; Jayaram, B. Eur. J. Med. Chem., 2017, 136, 36-51.
[http://dx.doi.org/10.1016/j.ejmech.2017.04.064] [PMID: 28478343]
[21]
Porter, D.W.; Bradley, M.; Brown, Z.; Canova, R.; Charlton, S.; Cox, B.; Hunt, P.; Kolarik, D.; Lewis, S.; O’Connor, D.; Reilly, J.; Spanka, C.; Tedaldi, L.; Watson, S.J.; Wermuth, R.; Press, N.J. Bioorg. Med. Chem. Lett., 2014, 24(1), 72-76.
[http://dx.doi.org/10.1016/j.bmcl.2013.11.074] [PMID: 24332493]
[22]
Yang, G-F.; Lu, R-J.; Fei, X-N.; Yang, H-Z. Chin. J. Chem., 2000, 18, 435-440.
[23]
Zhai, X.; Zhang, C-l.; He, L.; Li, Q.; Wang, J-l.; Shen, X-l.; Gong, P. Chem. Res. Chin. Univ., 2009, 25, 474-479.
[24]
Chen, C-N.; Lv, L-L.; Ji, F-Q.; Chen, Q.; Xu, H.; Niu, C-W.; Xi, Z.; Yang, G-F. Bioorg. Med. Chem., 2009, 17(8), 3011-3017.
[http://dx.doi.org/10.1016/j.bmc.2009.03.018] [PMID: 19342247]
[25]
Richardson, C.M.; Williamson, D.S.; Parratt, M.J.; Borgognoni, J.; Cansfield, A.D.; Dokurno, P.; Francis, G.L.; Howes, R.; Moore, J.D.; Murray, J.B.; Robertson, A.; Surgenor, A.E.; Torrance, C.J. Bioorg. Med. Chem. Lett., 2006, 16(5), 1353-1357.
[http://dx.doi.org/10.1016/j.bmcl.2005.11.048] [PMID: 16325401]
[26]
Chen, Q.; Zhu, X-L.; Jiang, L-L.; Liu, Z-M.; Yang, G-F. Eur. J. Med. Chem., 2008, 43(3), 595-603.
[http://dx.doi.org/10.1016/j.ejmech.2007.04.021] [PMID: 17618711]
[27]
Maybhate, S.P.; Rajamohanan, P.P.; Rajappa, S. Synthesis, 1991, 220-222.
[http://dx.doi.org/10.1055/s-1991-26426]
[28]
Ram, V.J.; Pratibha, S.; Singh, S.K.; Kandpal, M.; Tekwani, B.L. Bioorg. Med. Chem. Lett., 1997, 7, 1087-1090.
[http://dx.doi.org/10.1016/S0960-894X(97)00166-2]
[29]
Wang, H.; Lee, M.; Peng, Z.; Blázquez, B.; Lastochkin, E.; Kumarasiri, M.; Bouley, R.; Chang, M.; Mobashery, S. J. Med. Chem., 2015, 58(10), 4194-4203.
[http://dx.doi.org/10.1021/jm501831g] [PMID: 25923368]
[30]
Patel, D.C. Int. J. Sci. Res. Sci. Technol., 2017, 3, 666-673.
[31]
Amish, P.K. Int. J. Sci. Res. Sci. Technol., 2017, 3, 1281-1287.
[32]
Kumari, K.; Raghuvanshi, D.S.; Singh, K.N. Org. Prep. Proced. Int., 2012, 44, 460-466.
[http://dx.doi.org/10.1080/00304948.2012.715062]
[33]
Hassan, G.S.; El-Sherbeny, M.A.; El-Ashmawy, M.B.; Bayomi, S.M.; Maarouf, A.R.; Badria, F.A. Arab. J. Chem., 2017, 10(Suppl. 1), S1345-S1355.
[http://dx.doi.org/10.1016/j.arabjc.2013.04.002]
[34]
Tominaga, Y.; Sakai, S.; Kohra, S.; Tsuka, J.; Matsuda, Y.; Kobayashi, G. Chem. Pharm. Bull. (Tokyo), 1985, 33, 962-970.
[http://dx.doi.org/10.1248/cpb.33.962]
[35]
Peng, H.; Kumaravel, G.; Yao, G.; Sha, L.; Wang, J.; Van Vlijmen, H.; Bohnert, T.; Huang, C.; Vu, C.B.; Ensinger, C.L.; Chang, H.; Engber, T.M.; Whalley, E.T.; Petter, R.C. J. Med. Chem., 2004, 47(25), 6218-6229.
[http://dx.doi.org/10.1021/jm0494321] [PMID: 15566292]
[36]
Krasovskiy, A.L.; Moiseev, A.M.; Nenajdenko, V.G.; Balenkova, E.S. Synthesis, 2002, 901-905.
[http://dx.doi.org/10.1055/s-2002-28512]
[37]
Shaaban, M.R.; Saleh, T.S.; Mayhoub, A.S.; Mansour, A.; Farag, A.M. Bioorg. Med. Chem., 2008, 16(12), 6344-6352.
[http://dx.doi.org/10.1016/j.bmc.2008.05.011] [PMID: 18502132]
[38]
Čebašek, P.; Bevk, D.; Pirc, S.; Stanovnik, B.; Svete, J. J. Comb. Chem., 2006, 8(1), 95-102.
[http://dx.doi.org/10.1021/cc050073k] [PMID: 16398559]
[39]
Lipunova, G.N.; Nosova, E.V.; Laeva, A.A.; Kodess, M.I.; Charushin, V.N. Russ. J. Org. Chem., 2005, 41, 1071-1080.
[http://dx.doi.org/10.1007/s11178-005-0295-7]
[40]
Lahmidi, S.; Anouar, E.H.; El Hafi, M.; Boulhaoua, M.; Ejjoummany, A.; El Jemli, M.; Essassi, E.M.; Mague, J.T. J. Mol. Struct., 2019, 1177, 131-142.
[http://dx.doi.org/10.1016/j.molstruc.2018.09.046]
[41]
Zarguil, A.; Boukhris, S.; El Efrit, M.L.; Souizi, A.; Essassi, E.M. Tetrahedron Lett., 2008, 49, 5883-5886.
[http://dx.doi.org/10.1016/j.tetlet.2008.07.134]
[42]
Abdel-Latif, N.A. Sci. Pharm., 2005, 73, 193-216.
[http://dx.doi.org/10.3797/scipharm.aut-05-15]
[43]
Rashad, A.E.; Heikal, O.A.; El-Nezhawy, A.O.H.; Abdel-Megeid, F.M.E. Heteroatom Chem., 2005, 16, 226-234.
[http://dx.doi.org/10.1002/hc.20114]
[44]
Ram, V.J. J. Prakt. Chem., 1989, 331, 893-905.
[http://dx.doi.org/10.1002/prac.19893310603]
[45]
Ram, V.J.; Berghe, D.A.V.; Vlietinck, A.J. J. Heterocycl. Chem., 1984, 21, 1307-1312.
[http://dx.doi.org/10.1002/jhet.5570210513]
[46]
Vas’kevich, R.I.; Savitskii, P.V.; Zborovskii, Y.L.; Staninets, V.I.; Rusanov, E.B.; Chernega, A.N. Russ. J. Org. Chem., 2006, 42, 1403-1408.
[http://dx.doi.org/10.1134/S1070428006090272]
[47]
Kurbatov, E.S.; Starikova, Z.A.; Krasnikov, V.V.; Mezheritskii, V.V. Chem. Heterocycl. Compd., 2006, 42, 1366-1367.
[http://dx.doi.org/10.1007/s10593-006-0250-8]
[48]
Guetzoyan, L.J.; Spooner, R.A.; Lord, J.M.; Roberts, L.M.; Clarkson, G.J. Eur. J. Med. Chem., 2010, 45(1), 275-283.
[http://dx.doi.org/10.1016/j.ejmech.2009.10.007] [PMID: 19883956]
[49]
Johnson, T.C.; Martin, T.P.; Mann, R.K.; Pobanz, M.A. Bioorg. Med. Chem., 2009, 17(12), 4230-4240.
[http://dx.doi.org/10.1016/j.bmc.2009.02.010] [PMID: 19464188]
[50]
Abu-Hashem, A.A.; Gouda, M.A. J. Heterocycl. Chem., 2017, 54, 850-858.
[http://dx.doi.org/10.1002/jhet.2645]
[51]
Kamal, R.; Kumar, V.; Kumar, R.; Bhardwaj, J.K.; Saraf, P.; Kumari, P.; Bhardwaj, V. Arch. Pharm., 2017, 350e1700137
[http://dx.doi.org/10.1002/ardp.201700137]
[52]
J. Heterocycl. Chem., 1985, 22, 1607-1609.
[53]
Kreher, R.; Bergman, U. Tetrahedron Lett., 1976, •••, 4259-4262.
[http://dx.doi.org/10.1016/0040-4039(76)80089-5]
[54]
Giorgi, I.; Bianucci, A.M.; Biagi, G.; Livi, O.; Scartoni, V.; Leonardi, M.; Pietra, D.; Coi, A.; Massarelli, I.; Nofal, F.A.; Fiamingo, F.L.; Anastasi, P.; Giannini, G. Eur. J. Med. Chem., 2007, 42(1), 1-9.
[http://dx.doi.org/10.1016/j.ejmech.2006.08.014] [PMID: 17028066]
[55]
Mohamed, A.M.; Al-Qalawi, H.R.M.; El-Sayed, W.A.; Arafa, W.A.A.; Alhumaimess, M.S.; Hassan, A.K. Acta Pol. Pharm., 2015, 72(2), 307-318.
[PMID: 26642681]
[56]
Giorgi, I.; Biagi, G.; Bianucci, A.M.; Borghini, A.; Livi, O.; Leonardi, M.; Pietra, D.; Calderone, V.; Martelli, A. Eur. J. Med. Chem., 2008, 43(8), 1639-1647.
[http://dx.doi.org/10.1016/j.ejmech.2007.10.021] [PMID: 18045744]
[57]
Saundane, A.R.; Halu, A.; Kirankumar, N.M. Monatsh. Chem., 2017, 148, 1497-1511.
[http://dx.doi.org/10.1007/s00706-017-1957-1]