鎮痛剤の合成研究(第53報)3-(4-Substituted phenyl)-2-oxobutanamide誘導体の合成(複素環式化合物の合成研究第845報)

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Derivatives of 3-[4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl) phenyl]-2-oxobutanamide (1), exhibiting potent anti-inflammatory and analgesic activity, were obtained from 3-(4-aminophenyl)-2-oxo-butanamide (2) and 3-[4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl) phenyl]-2-oxobutanoic acid (25) as intermediates. Furthermore, the structures of E and Z isomers of 2-butenoic acid and oxiranecarboxylic acid derivatives as synthetic intermediates of compound (2) were studied. Among the derivatives, 3-[4-(2,5-dihydro-1H-pyrrol-1-yl) phenyl]-2-oxobutanamide (6), 2-oxo-3-[4-(1-piperidinyl) phenyl] butanamide (8), 3-[4-(3-carboxypropanoylamino)-phenyl]-2-oxobutanamide (11), 3-[4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-2-oxobutanamide (14), and N-benzyl-3-[4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl) phenyl]-2-oxobutanamide (16) showed potent anti-inflammatory activity comparable to phenylbutazone at the first screening with carragenin-induced rat paw edema.
社団法人日本薬学会の論文
1980-06-25