Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones

被引：34
作者：
Emami, Saeed [1 ,2 ]
Shojapour, Shahaboddin [1 ,2 ]
Faramarzi, Mohammad Ali [3 ,4 ]
Samadi, Nasrin [5 ,6 ]
Irannejad, Hamid [1 ,2 ]
机构：
[1] Mazandaran Univ Med Sci, Fac Pharm, Dept Med Chem, Sari, Iran
[2] Mazandaran Univ Med Sci, Fac Pharm, Pharmaceut Sci Res Ctr, Sari, Iran
[3] Univ Tehran Med Sci, Fac Pharm, Dept Pharmaceut Biotechnol, Tehran, Iran
[4] Univ Tehran Med Sci, Biotechnol Res Ctr, Tehran, Iran
[5] Univ Tehran Med Sci, Dept Drug & Food Control, Fac Pharm, Tehran, Iran
[6] Univ Tehran Med Sci, Pharmaceut Qual Assurance Res Ctr, Tehran, Iran
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 66卷
关键词：
Azole antifungals; Antifungal activity; 1,2,4-Triazole; Flavanones; Docking study; Drug-likeness; STEROL; 14-ALPHA-DEMETHYLASE; DERIVATIVES; AGENTS;
D O I：
10.1016/j.ejmech.2013.06.008
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of novel 3-(1,2,4-triazol-1-yl)flavanones were synthesized based on the N-phenethylazole pharmacophore of azole antifungals. The results of antifungal assay revealed that 4'-fluoroflavanone derivative 4c exhibited the best profile of activity against Candida and Saccharomyces strains. Compound 4c was 4-16 times more potent than reference drug fluconazole against Candida albicans and Saccharomyces cerevisiae. The molecular docking study with lanosterol 14 alpha-demethylase, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents. The favorable drug-like property of compound 4c makes 3-(1,2,4-triazol-1-yl)flavanone prototype as a promising lead for the future development of azole antifungal agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码：480 / 488
页数：9
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