Syntheses of 3-substituted pyrrole derivatives with antiinflammatory activity.

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Abstract
Various dimethyl 3-substituted pyrrole-2,4-dicarboxylates (3) were synthesized by the reaction of methyl isocyanoacetate with methyl .alpha.-isocyanoacrylates in the presence of base. This type of reaction was applicable to the preparation of 3-substituted pyrrole-2,4-dicarboxamides by employing appropriate amide compounds as reactants. Hydrolysis followed by decarboxylation of the pyrrole diester compounds (3) gave 3-substituted pyrroles (14) in good yields. A series of these compounds (14) showed antiinflammatory activities against carrageenan-induced rat paw edema. Among the compounds tested, 3-(2-chlorophenyl)pyrrole was more potent than mefenamic acid.