Synthesis and antimycotic activity of alpha-aryl-beta,N-imidazolylalkyl benzyl ethers

A new series of alpha-aryl-beta,N-imidazolylalkyl benzyl ethers was synthesized and tested for antimycotic and antimicrobial activity. Most of the compounds was highly active in vitro against fungi and gram-positive bacteria. The alpha,4-phenylthiophenyl-beta,N-imidazolylethyl benzyl ether (7) and the alpha,4-biphenyl-beta,N-imidazolylethyl benzyl ether (17) showed higher antifungal activity than 1-[2,4,dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole (miconazole) against Candida albicans. None of the compounds was more active than miconazole against Trichophyton mentagrophytes. The most interesting compounds of the series were assayed in vivo, but their activity was inconstant and always lower than that of miconazole.