Syntheses of 2-mercapto-4-substituted imidazole derivatives with antiinflammatory properties.

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Abstract
Various 2-mercapto-4-substituted-5-imidazolecarboxylates (5) were synthesized by the reaction of C-acylamino acid methyl esters with potassium thiocyanate. Hydrolysis followed by decarboxylation of the imidazole carboxylates (5) gave 2-mercapto-4-substituted imidazoles (8) in good yields. The imidazoles (8) were also directly obtained by the reaction of aminoketones with potassium thiocyanate. These compounds (8) exhibited antiinflammatory activities against carrageenan-induced rat paw edema. Among the compounds tested, 2-mercapto-4-(3-thienyl)imidazole (8r) showed the best therapeutic index value, giving a value comparable to that of mefenamic acid.

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