Synthesis and antifungal activities of a series of (1,2-disubstituted vinyl)imidazoles.
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.
Ogawa
M
M
Central Research Laboratories, SS Pharmaceutical Co., Ltd., Chiba, Japan.
Matsuda
H
H
Eto
H
H
Asaoka
T
T
Kuraishi
T
T
Iwasa
A
A
Nakashima
T
T
Yamaguchi
K
K
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D014961:X-Ray Diffraction
D000935:Antifungal Agents; D007093:Imidazoles; D014753:Vinyl Compounds