Synthesis and antifungal evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase

A series of 1-(1 H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols ( 1a– v, 2a– w), which are analogues of fluconazole, have been designed and synthesized as the potential antifungal agents by the click reaction. Click reaction approach toward the synthesis of two sets of novel...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2010-10, Vol.45 (10), p.4435-4445
Main Authors: Yu, Shichong, Chai, Xiaoyun, Hu, Honggang, Yan, Yongzheng, Guan, Zhongjun, Zou, Yan, Sun, Qingyan, Wu, Qiuye
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal activity
Antifungal agents
Biological and medical sciences
Click reaction
CYP51
Medical sciences
Pharmacology. Drug treatments
Synthesis
Triazole
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Summary:A series of 1-(1 H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols ( 1a– v, 2a– w), which are analogues of fluconazole, have been designed and synthesized as the potential antifungal agents by the click reaction. Click reaction approach toward the synthesis of two sets of novel 1,2,3-triazolyl linked triazole antifungal derivatives 1a– v, 2a– w was achieved by Cu(I)-catalyzed 1,3-dipolar cycloaddition of propargylated intermediate 8 with substituted azidomethyl benzene. The 1,2,3-triazolyl group was inserted into the side chain of the target molecule which can increase the antifungal activity of compounds. A number of novel triazole derivatives have been designed, synthesized by click reaction. And their antifungal activities have been evaluated against eight human pathogenic fungi. [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2010.07.002