期刊
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
卷 29, 期 2, 页码 263-271出版社
TAYLOR & FRANCIS LTD
DOI: 10.3109/14756366.2013.776554
关键词
Antifungal activity; azole antifungals; chroman-4-one; docking study; imidazole; lanosterol 14 alpha-demethylase
资金
- Research Council of Mazandaran University of Medical Sciences, Sari, Iran
Previously, 2-alkylchromans have been introduced as non-azole inhibitors of 14 alpha-demethylase. Accordingly, we incorporated imidazole ring on the 3-position of 2-alkylchromanones to design new inhibitors of 14 alpha-demethylase and potential antifungal agents. Thus, a series of 2-alkyl-3-imidazolylchromanones were synthesized starting from 2-hydroxyphenacyl bromide. The transconfiguration of compounds was confirmed by NMR-spectroscopy. The antifungal activity of title compounds were evaluated against different fungi in comparison with fluconazole and miconazole. trans-2-(1-Pentyl)-3-imidazolylchroman-4-one (4d) showed the most potent activity against yeasts comparable to fluconazole. The experimental data based on H-1 NMR spectroscopy revealed that 2-alkyl side chain and 3-imidazolyl moiety in compound 4d exist predominantly in the di-equatorial conformation. While docking study with 14 alpha-demethylase demonstrated that the di-axial form of compound 4d can be considered as active conformation.
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