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Antifungal activity of enynediesters and acetylenic compounds obtained by synthesis and in silico prediction pattern.

Abstract：

OBJECTIVE:In this paper, we describe the preparation and synthesis of several enynediesters, conjugated diynes and acetylenic compounds from starting materials comprising one hydroxyl and one acetylenyl group and their antifungal activity. MATERIALS AND METHODS:For synthesis of the compounds, a combined solution of N,N'-dicyclohexylcarbodiimide and 4-dimethylaminopyridin in CH2Cl2 was added to a solution of compound containing one hydroxyl group and propiolic acid at 0°C over a period of 1 hour. As the reaction occurs under very mild conditions this procedure offers easy access to 1,3-diynes in a very short reaction time. Some of the compounds are commercially available. The antifungal activity of these compounds against Candida albicans, Aspergillus niger and Saccharomyces cerevisiae was investigated. RESULTS:Among the compounds tested, some showed potent activity. CONCLUSION:The results of synthesis showed that the direct coupling of two acetylenes is suitable for the preparation of diynes. The in silico study used here was able to predict if the compound with triple bond can posses the antifungal activity with a reasonable prediction. The result of investigations at both in silico and in vitro levels confirmed that the position of the triple bond is important for antifungal activity.

journal_name

J Mycol Med

journal_title

Journal de mycologie medicale

authors

Azerang P,Sardari S

doi

10.1016/j.mycmed.2012.06.001

subject

Has Abstract

pub_date

2012-09-01 00:00:00

pages

230-6

issue

3

eissn

1156-5233

issn

1773-0449

pii

S1156-5233(12)00065-0

journal_volume

22

pub_type

杂志文章

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