Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives

European Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2011, Pages 3142-3148

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

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

1,2,4 Triazole; Antifungal activity; Piperazine; Synthesis

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL] 2,2 DIFLUOROACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL] 2,22, TRIFLUOROACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL] ACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL]BUTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL]ISOBUTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL]PROPIONAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]DODECANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PALMITAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL] 2,2 DIFLUOROACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL] 2,2,2 TRIFLUOROACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]ACETAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]BUTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]DECANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]HEPTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]HEXANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]ISOBUTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]OCTANAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]PIVALAMIDE; 2 CHLORO N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL]PHENYL]PROPIONAMIDE; AMPHOTERICIN B; ANTIFUNGAL AGENT; FLUCONAZOLE; ITRACONAZOLE; KETOCONAZOLE; N [4 [4 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]PIPERAZIN 1 YL] 3 FLUOROPHENYL]ACETAMIDE; PIPERAZINE DERIVATIVE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VORICONAZOLE; 1,2,4-TRIAZOLE; CYTOCHROME P450 INHIBITOR; FUNGAL PROTEIN; TRIAZOLE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ARTHRODERMA GYPSEUM; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA PARAPSILOSIS; CANDIDA TROPICALIS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME STRUCTURE; FONSECAEA; FONSECAEA COMPACTA; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; TRICHOPHYTON RUBRUM; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CATALYTIC DOMAIN; CRYPTOCOCCUS NEOFORMANS; CYTOCHROME P-450 ENZYME INHIBITORS; DRUG DESIGN; FLUCONAZOLE; FUNGAL PROTEINS; MICROBIAL SENSITIVITY TESTS; MOLECULAR DOCKING SIMULATION; PIPERAZINES; STEROL 14-DEMETHYLASE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; VORICONAZOLE;

EID: 79957470103     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.02.042     Document Type: Article

References (15)

1. A. Amorim, L.G. Vazc, and R. Araujo Int. J. Antimicrob. Ag 35 2010 396 399
2. E. Giavini, and E. Menegola Toxicol. Lett. 198 2010 106 111
3. N. Kiraz, I. Dag, Y. Oz, M. Yamac, A. Kiremitci, and N. Kasifoglu J. Microbiol. Meth. 82 2010 136 140
4. X. Chai, J. Zhang, H. Hu, Sh. Yu, Q. Sun, Zh. Dan, Y. Jiang, and Q. Wu Eur.J.Med.Chem. 44 2009 1913 1920
5. N. Robbins, C. Collins, J. Morhayim, and L.E. Cowen Fungal Genet. Biol. 47 2010 81 93
6. P.E. Verweija, S.J. Howardb, W.J.G. Melchersa, and D.W. Denning Drug Resist. Update 12 2009 141 147
7. L. Xiao, V. Madison, A.S. Chau, D. Loebenberg, R.E. Palermo, and P.M. McNicholas Antimicrob. Agents Ch 48 2004 568 574
8. S.H. Chen, C.Q. Sheng, X.H. Xu, W.N. Zhang, and C. He Biol. Pharm. Bull. 30 2007 1246 1253
9. H. Ji, W. Zhang, Y. Zhou, M. Zhang, J. Zhu, Y. Song, and J. Lu J. Med. Chem. 43 2000 2493 2505
10. Q. Sun, C. Liu, Q. Wu, D. Zhang, Y. Cao, Y. Jiang, and H. Zhao Zhongguo Yaowu Huaxue Zazhi 14 2004 14 18
11. Q. Sun, W. Zhang, J. Xu, Y. Cao, Q. Wu, D. Zhang, C. Liu, Sh. Yu, and Y. Jiang Eur. J. Med. Chem. 42 2007 1151 1157
12. Q. Sun, J. Xu, Y. Cao, W. Zhang, Q. Wu, D. Zhang, J. Zhang, H. Zhao, and Y. Jiang Eur. J. Med. Chem. 42 2007 1226 1233
13. K. Richardson, US Patent 4,404,216, 1983.
14. National Committee for Clinical Laboratory Standards Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts Approved Standard. Document M27-A2 2002 National Committee for Clinical Laboratory Standards Wayne, PA
15. C. Sheng, W. Zhang, H. Ji, M. Zhang, Y. Song, H. Xu, J. Zhu, Z. Miao, Q. Jiang, J. Yao, Y. Zhou, J. Zhu, and J. Lü J. Med. Chem. 49 2006 2512 2515