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

European Journal of Medicinal Chemistry

Volumn 46, Issue 7, 2011, Pages 3135-3141

  Jiang, Yongwei ^a   Cao, Yongbin ^a   Zhang, Jun ^a   Zou, Yan ^a   Chai, Xiaoyun ^a   Hu, Honggang ^a   Zhao, Qingjie ^a   Wu, Qiuye ^a   Zhang, Dazhi ^a   Jiang, Yuanying ^a   Sun, Qingyan ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

1H 1,2,4 triazol 5(4H) one derivatives; Antifungal evaluation; Synthesis

Indexed keywords

1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (4 FLUOROPHENYL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (4 METHYLPYRIDIN 2 YL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (4 NITROPHENYL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (4 TOLYL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (5 METHYLPYRIDIN 2 YL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 (THIAZOL 2 YL) 1H 1,2,4 TRIAZOL 5(4H) ONE; 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 PHENYL 1H 1,2,4 TRIAZOL 5(4H) ONE; 1,2,4 TRIAZOLE DERIVATIVE; 3 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 5(4H) YL]BENZONITRILE; 4 (2 CHLOROPHENYL) 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 PHENYL 1H 1,2,4 TRIAZOL 5(4H) ONE; 4 (3,4 DICHLOROPHENYL) 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL]1H 1,2,4 TRIAZOL 5(4H) ONE; 4 (4 AMINOPHENYL) 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 PHENYL 1H 1,2,4 TRIAZOL 5(4H) ONE; 4 (4 BROMOPHENYL) 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 PHENYL 1H 1,2,4 TRIAZOL 5(4H) ONE; 4 (4 CHLOROPHENYL) 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 4 PHENYL 1H 1,2,4 TRIAZOL 5(4H) ONE; 4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 5(4H) YL]BENZONITRILE; 4 [4 (2,4 DICHLOROPHENYL)THIAZOL 2 YL] 1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 1H 1,2,4 TRIAZOL 5(4H) ONE; AMPHOTERICIN B; ANTIFUNGAL AGENT; FLUCONAZOLE; FLUCONAZOLE DERIVATIVE; ITRACONAZOLE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]ACETAMIDE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]BUTYRAMIDE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]HEPTANAMIDE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]HEXANAMIDE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]PENTANAMIDE; N [4 [1 [2 (2,4 DIFLUOROPHENYL) 2 HYDROXY 3 (1H 1,2,4 TRIAZOL 1 YL)PROPYL] 5 OXO 1H 1,2,4 TRIAZOL 4(5H) YL]PHENYL]PROPIONAMIDE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VORICONAZOLE; CYTOCHROME P450 INHIBITOR; FUNGAL PROTEIN; TRIAZOLE DERIVATIVE;

ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA PARAPSILOSIS; CANDIDA TROPICALIS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ACTIVE SITE; INFRARED SPECTROSCOPY; KLUYVEROMYCES MARXIANUS; MASS SPECTROMETRY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON RUBRUM; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; SYNTHESIS;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CYTOCHROME P-450 ENZYME INHIBITORS; DRUG DESIGN; FLUCONAZOLE; FUNGAL PROTEINS; MICROBIAL SENSITIVITY TESTS; STEROL 14-DEMETHYLASE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 79957522536     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.02.001     Document Type: Article

References (17)

1. L. Helen, A. Leather, R. John, and B. Wingard Blood Rev. 20 2006 267 287
2. S.K. Fridkin, and W.R. Jarvis Clin. Microbiol. Rev. 9 1996 499 511
3. D.J. Sheehan, C.A. Hitchcock, and C.M. Sibley Clin. Microbiol. Rev. 12 1999 40
4. X.Y. Chai, J. Zhang, H.G. Hu, S.C. Yu, Q.Y. Sun, Z.G. Dan, Y.Y. Jiang, and Q.Y. Wu Euro. J. Med. Chem. 44 2009 1913 1920
5. N.H. Georgopapadakou, and T.J. Walsh Antimicrob. Agents Chemother. 40 1996 279
6. E. Ben de Pauw, and J. Juan Picazo Antimicrob. Agents 32 2008 S167 S171
7. Y. Yoshida, Y. Aoyama, M. Noshiro, and O. Gotoh Biochem. Biophys. Res. Commun. 273 2000 799 804
8. Y. Aoyama, M. Noshiro, O. Gotoh, S. Imaoka, Y. Funae, N. Kurosawa, T. Horiuchi, and Y. Yoshida J. Biochem. 119 1996 926 933 (Tokyo)
9. D.R. Nelson Arch. Biochem. Biophys. 369 1999 1 10
10. R.T. Fischer, J.M. Trzaskos, R.L. Magolda, S.S. Ko, C.S. Brosz, B. Larsen, and J. Biol Chem. 266 1991 6124 6132
11. H. Ji, W. Zhang, Y. Zhou, M. Zhang, J. Zhu, Y. Song, J. Lu, and J. Med Chem. 43 2000 2493
12. D.F. Lewis, A. Wiseman, M.H. Tarbit, and J. Enzym Inhib. 14 1999 175 192
13. K. Richardson US Patent 4404216 1983
14. N. Krishnamurthy, and J. James US Patent 5728834A 1998
15. 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
16. E. Mellado, G. Garcia-Effron, L. Alca′zar-Fuoli, W.J.G. Melchers, P.E. Verweij, M. Cuenca-Estrella, and J.L. Rodriguez-Tudela Antimicrob. Agents Chemother. 51 2007 1897
17. R.A. Calderone Candida and Candidiasis 2002 Asm Press Washington, DC