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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., (Copyright © 2012 Elsevier Masson SAS. All rights reserved.)

A series of oligoesters based on a rigid triphenyl-diyne core is described. The molecules were readily synthesized from key intermediates, and retained good solubility properties. One of the compounds displayed modest ion transport activity in vesicles, was capable of forming highly conducting single channels in planar bilayers and exhibited an irregular non-linear current-voltage response. All the reported molecules had minimal aqueous fluorescence while being highly fluorescent in less-polar media including lipid vesicles; their partitioning into the membrane could be monitored by a significant blue-shift and increase in fluorescence intensity, as well as a decreased extent of quenching in vesicles over that in water. The combined data indicated that the compounds are highly aggregated in aqueous solution, which limits their membrane partitioning and ion transport activity, in agreement with mechanisms proposed for other 'simple' oligoester channels.