title: Synthesis and antifungal activities of a series of (1,2-disubstituted vinyl)imidazoles.
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.
authors.affiliation: Central Research Laboratories, SS Pharmaceutical Co., Ltd., Chiba, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Ogawa
authors.forename: H
authors.initials: H
authors.lastname: Matsuda
authors.forename: H
authors.initials: H
authors.lastname: Eto
authors.forename: T
authors.initials: T
authors.lastname: Asaoka
authors.forename: T
authors.initials: T
authors.lastname: Kuraishi
authors.forename: A
authors.initials: A
authors.lastname: Iwasa
authors.forename: T
authors.initials: T
authors.lastname: Nakashima
authors.forename: K
authors.initials: K
authors.lastname: Yamaguchi
mesh_terms: 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
chemical_list: D000935:Antifungal Agents; D007093:Imidazoles; D014753:Vinyl Compounds