新規抗炎症剤4′-Acetyl-2′-(2,4-difluorophenoxy) methanesulfonanilide(FK3311)代謝物の立体選択的合成とその薬理作用

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Asymmetric reduction of acetophenone (FK3311 : 1) and ethyl phenylglyoxylate (7) with various chiral reducing agents was investigated in an attempt to synthesize both optical isomers of the two metabolites (2 and 5) of 1. The treatment of 1 with 3,3-diphenyl-1-methyltetrahydro-1H, 3H-pyrrolo[1,2-c]-[1,3,2]-oxazaborolidine-borane complex (reductants B, C) gave chiral alcohol 2 in a high optical purity. On the other hand, reduction of 7 by B-chlorodiisopinocamphenylborane (reductants E, F) gave the best result among the tested reagents. Each isomer of 2 and 5 was examined for in vitro activity to inhibit zymosan-induced prostaglandine E_2 production, adjuvant-induced arthritis for antiinflammatory activity, and acetic acid-induced writhing for analgesic activity in comparison with the racemic mixture.
社団法人日本薬学会の論文
1995-11-25