Aliphatic ethers of 1-(2,4-dichlorophenyl)-2-(1-H-imidazolyl)ethanol: Influence of ramification and/or unsaturation on lipophilicity and antifungal activity

Article abstract of DOI:10.1016/S0223-5234(97)89644-4

Ethers of 1-(2,4-dichlorophenyl)-2-(1-H-imidazolyl)ethanol bearing influence ramification and/or unsaturated chains have been synthesized in order to specify the role of lipophilicity or steric contributions on antifungal activity against yeast for miconazole-like structures. The presence of ramifications on aliphatic chains (between 4 and 7 carbons) or unsaturation at the end, increases antifungal activity. For these compounds, lipophilicity seems to be counterbalanced by steric contributions.