Synthesis and Antiallergic Activities of 2-Alkyl-3,4-dimethylfuro[2,3-c]pyrazole-5-carboxamides and Related Compounds
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概要
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A series of 2-substituted 3,4-dimethylfuro[2,3-c]pyrazole-5-carboxamides and related compounds have been synthesized and their antiallergic activities were evaluated. Most derivatives with a lower alkyl group at position 2 were orally active. Among them, N-ethyl-2,3,4-trimethylfuro[2,3-c]pyrazole-5-carboxamide (III_3), 2-ethyl-N-methyl-3,4-dimethylfuro[2,3-c]pyrazole-5-carboxamide (III_<14>), 2-isopropyl-N-methyl-3,4-dimethylfuro[2,3-c]pyrazole-5-carboxamide (III_<27>), 5-(4,5-dihydro-5-oxo-1,3,4-oxadiazol-2-yl)-2,3,4-trimethylfuro[2,3-c]pyrazole (IV_1) and 5-(4,5-dihydro-5-oxo-1,3,4-oxadiazol-2-yl)-2-isopropyl-3,4-dimethylfuro[2,3-c]pyrazole (IV_3) showed promising antial-lergic effects. The structure-activity relation of these 3,4-dimethylfuro[2,3-c]pyrazole derivatives was examined. An amide or 5-oxo-1,3,4-oxadiazole substituent at position 5 was favorable, while introduction of a carboxylic acid or acrylic acid moiety was unfavorable. However, none of these compounds exerted a significant inhibitory effect on mast cell degranulation. Compound III_<27> and IV_3 showed potent anti-allergic activity. We found that they also suppressed histamine-, serotonin-, bradykinin- and substance P-induced ear edema in mice. In compound 48/80-pretreated mice, the preformed mediators in mast cells in the ear were greatly reduced. Under this condition, the bradykinin- and substance P-induced ear edema was suppressed by compound III_<27> and IV_3 to a significantly greater extent than by diphenhydramine combined with methylsergide. These results indicated that the antiallergic effect of 3,4-dimethylfuro[2,3-c]pyrazole derivatives probably involves protection of the vasculature against the effects of challenge by several mediators.
- 公益社団法人日本薬学会の論文
- 1994-10-15
著者
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中村 秀雄
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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黄 麗嬌
Graduate Institute Of Pharmaceutical Chemistry China Medical College
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郭 盛助
Graduate Institute Of Pharmaceutical Chemistry China Medical College
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石井 勝美
Research Laboratories Dainippon Pharmaceutical Co. Ltd.
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王 繼平
Department of Medical Research, Taichung Veterans General Hospital
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王 繼平
Department Of Medical Research Taichung Veterans General Hospital
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