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Synthesis and Evaluation of Some Substituted Heterocyclic Fluconazole Analogues as Antifungal Agents
Corresponding Author(s) : Shichong Yu
Asian Journal of Chemistry,
Vol. 26 No. 8 (2014): Vol 26 Issue 8
Abstract
A new series of fluconazole analogues of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluoro-phenyl)-3-4-(substituted-heterocyclic ring-1H-1,2,3-triazol-1-yl)-2-propanols (1-10) were designed, synthesized and evaluated as antifungal agents. Preliminary antifungal tests showed that most of the title compounds exhibited moderate activity with broad spectrum against eight human pathogenic fungi in vitro, compounds 1 and 6 had the best antifungal activity against Candida albicans with the value of MIC80 = 0.5 μg/mL respectively.
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- P.G. Pappas, B.D. Alexander, D.R. Andes, S. Hadley, C.A. Kauffman, A. Freifeld, E.J. Anaissie, L.M. Brumble, L. Herwaldt, J. Ito, D.P. Kontoyiannis, G.M. Lyon, K.A. Marr, V.A. Morrison, B.J. Park, T.F. Patterson, T.M. Perl, R.A. Oster, M.G. Schuster, R. Walker, T.J. Walsh, K.A. Wannemuehler and T.M. Chiller, Clin. Infect. Dis., 50, 1101 (2010); doi:10.1086/651262.
- M.D. Richardson, J. Antimicrob. Chemother., 56(suppl 1), 5 (2005); doi:10.1093/jac/dki218.
- D.W. Warnock, Nippon Ishinkin Gakkai Zasshi, 48, 1 (2007); doi:10.3314/jjmm.48.1.
- C. Garcia-Vidal, D. Viasus and J. Carratalà, Curr. Opin. Infect. Dis., 26, 270 (2013); doi:10.1097/QCO.0b013e32835fb920.
- M.H. Miceli, J.A. Díaz and S.A. Lee, Lancet Infect. Dis., 11, 142 (2011); doi:10.1016/S1473-3099(10)70218-8.
- J.R. Wingard and H. Leather, Biol. Blood Marrow Transplant., 10, 73 (2004); doi:10.1016/j.bbmt.2003.09.014.
- S.K. Fridkin and W.R. Jarvis, Clin. Microbiol. Rev., 9, 499 (1996).
- M.A. Pfaller, Am. J. Med., 125, S3 (2012); doi:10.1016/j.amjmed.2011.11.001.
- D.S. Johnson and J.J. Li, The Art of Drug Synthesis, 7, 71 (2007).
- M. Canuto and F. Rodero, Lancet Infect. Dis., 2, 550 (2002); doi:10.1016/S1473-3099(02)00371-7.
- T. Konosu, Y. Tajima, N. Takeda, T. Miyaoka, M. Kasahara, H. Yasuda and S. Oida, Chem. Pharm. Bull. (Tokyo), 38, 2476 (1990); doi:10.1248/cpb.38.2476.
- S.C. Yu, X.Y. Chai, H. Hu, Y. Yan, Z. Guan, Y. Zou, Q. Sun and Q. Wu, Eur. J. Med. Chem., 45, 4435 (2010); doi:10.1016/j.ejmech.2010.07.002.
- B.G. Wang, S.C. Yu, X.Y. Chai, Y.Z. Yan, H.G. Hu and Q.Y. Wu, Chin. Chem. Lett., 22, 519 (2011); doi:10.1016/j.cclet.2010.11.029.
- Y. Zou, Q. Zhao, J. Liao, H. Hu, S. Yu, X. Chai, M. Xu and Q. Wu, Bioorg. Med. Chem. Lett., 22, 2959 (2012); doi:10.1016/j.bmcl.2012.02.042.
- National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts Approved standard. Document M27-A2, National Committee for Clinical Laboratory Standards, Wayne, PA (2002).
References
P.G. Pappas, B.D. Alexander, D.R. Andes, S. Hadley, C.A. Kauffman, A. Freifeld, E.J. Anaissie, L.M. Brumble, L. Herwaldt, J. Ito, D.P. Kontoyiannis, G.M. Lyon, K.A. Marr, V.A. Morrison, B.J. Park, T.F. Patterson, T.M. Perl, R.A. Oster, M.G. Schuster, R. Walker, T.J. Walsh, K.A. Wannemuehler and T.M. Chiller, Clin. Infect. Dis., 50, 1101 (2010); doi:10.1086/651262.
M.D. Richardson, J. Antimicrob. Chemother., 56(suppl 1), 5 (2005); doi:10.1093/jac/dki218.
D.W. Warnock, Nippon Ishinkin Gakkai Zasshi, 48, 1 (2007); doi:10.3314/jjmm.48.1.
C. Garcia-Vidal, D. Viasus and J. Carratalà, Curr. Opin. Infect. Dis., 26, 270 (2013); doi:10.1097/QCO.0b013e32835fb920.
M.H. Miceli, J.A. Díaz and S.A. Lee, Lancet Infect. Dis., 11, 142 (2011); doi:10.1016/S1473-3099(10)70218-8.
J.R. Wingard and H. Leather, Biol. Blood Marrow Transplant., 10, 73 (2004); doi:10.1016/j.bbmt.2003.09.014.
S.K. Fridkin and W.R. Jarvis, Clin. Microbiol. Rev., 9, 499 (1996).
M.A. Pfaller, Am. J. Med., 125, S3 (2012); doi:10.1016/j.amjmed.2011.11.001.
D.S. Johnson and J.J. Li, The Art of Drug Synthesis, 7, 71 (2007).
M. Canuto and F. Rodero, Lancet Infect. Dis., 2, 550 (2002); doi:10.1016/S1473-3099(02)00371-7.
T. Konosu, Y. Tajima, N. Takeda, T. Miyaoka, M. Kasahara, H. Yasuda and S. Oida, Chem. Pharm. Bull. (Tokyo), 38, 2476 (1990); doi:10.1248/cpb.38.2476.
S.C. Yu, X.Y. Chai, H. Hu, Y. Yan, Z. Guan, Y. Zou, Q. Sun and Q. Wu, Eur. J. Med. Chem., 45, 4435 (2010); doi:10.1016/j.ejmech.2010.07.002.
B.G. Wang, S.C. Yu, X.Y. Chai, Y.Z. Yan, H.G. Hu and Q.Y. Wu, Chin. Chem. Lett., 22, 519 (2011); doi:10.1016/j.cclet.2010.11.029.
Y. Zou, Q. Zhao, J. Liao, H. Hu, S. Yu, X. Chai, M. Xu and Q. Wu, Bioorg. Med. Chem. Lett., 22, 2959 (2012); doi:10.1016/j.bmcl.2012.02.042.
National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts Approved standard. Document M27-A2, National Committee for Clinical Laboratory Standards, Wayne, PA (2002).