Synthesis and Biological Evaluation of Triazole Derivatives as Potential Antifungal Agent

Chemical Biology and Drug Design

Volumn 80, Issue 3, 2012, Pages 382-387

  Chai, Xiaoyun ^a   Yang, Guang ^a   Zhang, Jun ^a   Yu, Shichong ^a   Zou, Yan ^a   Wu, Qiuye ^a   Zhang, Dazhi ^a   Jiang, Yuanying ^a   Cao, Yongbing ^a   Sun, Qingyan ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Antifungal agent; Molecular docking; Synthesis; Triazole

Indexed keywords

1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERIDIN 4 OL; ANTIFUNGAL AGENT; FLUCONAZOLE; ITRACONAZOLE; RAVUCONAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; BINDING SITE; BIOLOGICAL ACTIVITY; CANDIDA ALBICANS; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL;

ANTIFUNGAL AGENTS; CATALYTIC DOMAIN; FUNGI; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MYCOSES; PIPERIDINES; STEROL 14-DEMETHYLASE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

FUNGI;

EID: 84864119032     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01398.x     Document Type: Article

References (19)

1. Fridkin S.K., Jarvis W.R. (1996) Epidemiology of nosocomial fungal infections. Clin Microbiol Rev;9:499-511.
2. Wingard J.R., Leather H. (2004) A new era of antifungal therapy. Biol Blood Marrow Transplant;10:73-90.
3. Dismukes W.E. (2006) Antifungal therapy: lessons learned over the past 27years. Clin Infect Dis;42:1289-1296.
4. Goossens H. (2005) European status of resistance in nosocomial infections. Chemotherapy;51:177-181.
5. Heidemann H.T., Gerkens F.F., Spickard W.A., Jackson E.K., Branch R.A. (1983) Amph-otericin B nephrotoxicity in humans decreased by salt repletion. Am J Med;75:476-481.
6. Garcia-Rodriguez L.A., Duque A., Castellsague J., Pérez-Gutthann S., Stricker B. H. (1999) A cohort study on the risk of acute liver injury among users of ketoconazole and other antifungal drugs. Br J Clin Pharmacol;48:847-852.
7. Lavrijsen A. P., Balmus K. J., Nugteren-Huying W. M., Roldaan A. C., Van't Wout J. W., Stricker B. H. (1992) Hepatic injury associated with itraconazole. Lancet;340:251-252.
8. Georgopapadakou N.H., Walsh T.J. (1996) Antifungal agents: chemotherapeutic targets and immunologic strategies. Antimicrob Agents Chemother;40:279-291.
9. Chai X. Y., Zhang J., Yu S. C., Hu H. G., Zou Y., Zhao Q. J., Dan Z. G., Zhang D. Z., Wu Q. Y. (2009) Design, synthesis, and biological evaluation of novel 1-(1H-1, 2, 4-triazole-1-yl)-2-(2, 4-difluorophenyl)-3- substituted benzylam-ino-2-propanols. Bioorg Med Chem Lett;19:1811-1814.
10. Guan Z.J., Chai X.Y., Yu S.C., Hu H.G., Jiang Y.Y., Meng Q.G., Wu Q.Y. (2010) Synthesis, molecular docking and biological evaluation of novel triazole derivatives as antifungal agents. Chem Biol Drug Des;76:496-504.
11. Yu S.C., Chai X.Y., Hu H.G., Yan Y.Z., Guan Z.J., Zou Y., Sun Q.Y., Wu Q.Y. (2010) Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14a-demethylase. Eur J Med Chem;45:4435-4445.
12. Chai X.Y., Zhang J., Cao Y.B., Zou Y., Wu Q.Y., Zhang D.Z., Jiang Y.Y., Sun Q.Y. (2011) New azoles with antifungal activity: design, synthesis, and molecular docking. Bioorg Med Chem Lett;21:686-689.
13. Jiang Y.W., Cao Y.B., Zhang J., Zou Y., Chai X.Y., Hu H.G., Zhao Q.J., Wu Q.Y., Zhang D.Z., Jiang Y.Y., Sun Q.Y. (2011) Design, synthesis and antifungal evaluation of 1-(2-(2, 4-difluorophenyl)-2-hydroxy-3-(1H-1, 2, 4-triazol-1-yl)propyl)-1H-1, 2, 4-triazol-5(4H)-one. Eur J Med Chem;46:3135-3141.
14. Chai X.Y., Zhang J., Cao Y.B., Zou Y., Wu Q.Y., Zhang D.Z., Jiang Y.Y., Sun Q.Y. (2011) Design, synthesis and molecular docking studies of novel triazole as antifungal agent. Eur J Med Chem;46:3167-3176.
15. Sheng C.Q., Zhang W.N., Ji H.T., Song Y.L., Zhang M., Zhou Y.J., Lv J.G., Zhu J. (2004) Design, synthesis and antifungal activity of novel triazole derivatives. Chin Chem Lett;15:404-407.
16. Aoyama Y., Yoshida Y., Sonoda Y., Sato Y. (1987) Metabolism of 32-hydroxy-24, 25-dihydrolanosterol by purified cytochrome P-45014DM from yeast. Evidence for contribution of the cytochrome to whole process of lanosterol 14α-demethylation. J Biol Chem;262:1239-1243.
17. National Committee for Clinical Laboratory Standards (2002) Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts Approved Standard. Document M27-A2. Wayne, PA: National Committee for Clinical Laboratory Standards.
18. Ji H. T., Zhang W. N., Zhou Y. J., Zhang M., Zhu J., Song Y. L., Lü J. G., Zhu J. (2000) A three-dimensional model of lanosterol 14α-demthylase of Candida albicans and its interaction with azole antifungals. J Med Chem;43:2493-2505.
19. Sheng C.Q., Zhang W.N., Ji H.T., Zhang M., Song Y.L., Xu H., Zhu J., Miao Z.Y., Jiang Q.F., Yao J.Z., Zhou Y.J., Zhu J., Lv J.G. (2006) Structure-based optimization of azole antifungal agents by CoMFA, CoMSIA, and molecular docking. J Med Chem;49:2512-2525.