Synthesis and antifungal activities of a series of (1,2-disubstituted vinyl)imidazoles. |
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| Authors: | M Ogawa H Matsuda H Eto T Asaoka T Kuraishi A Iwasa T Nakashima K Yamaguchi |
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| Affiliation: | Central Research Laboratories, SS Pharmaceutical Co., Ltd., Chiba, Japan. |
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| Abstract: | A series of vinylimidazoles containing a hetero atom such as sulfur or oxygen at a beta-position of the vinyl group was prepared and the antifungal activities were tested. It was found that sulfur-substituted derivatives such as (E)-1-[2-(methylthio)-1-[2-(pentyloxy)phenyl]ethenyl]-1H-imidazole (5a-5) and (E)-1-[1-[2-(hexyloxy)phenyl]-2-(methylthio)ethenyl]-1H-imidazole (5a-6) showed excellent antifungal activities against dermatophytes and yeast cells. The stereochemistry of the hydrochloride salt of 5a-5 was determined by X-ray crystallography. The structure-activity relationships were discussed. |
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