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S-substituted derivatives of 1,2,4-triazol-3-thiol as new drug candidates for type II diabetes

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The therapeutic applications of 1,2,4-triazoles motivated us to synthesize some new derivatives. Two series of S -substituted derivatives (8a–8j, 12a–12i) of 5-{1-[(4-chlorophenyl)sulfonyl]-3-piperidinyl}-4-phenyl-4H -1,2,4-triazol3-thiol (6) have been synthesized and evaluated for their biological potential. Using 4-chlorobenzene sulfonyl chloride (1) and ethyl piperidine-3-carboxylate (2), ethyl 1-[(4-chlorophenyl)sulfonyl]piperidine-3-carboxylate (3) was synthesized and converted into 3,4,5-trisubstituted 1,2,4-triazole (6) through formation of the corresponding carbohydrazide (4) and hydrazinecarbothioamide (5). Compound 6 was transformed into 8a–8j by alkyl halides (7a–7j) and into 12a–12i by N-aralkyl/aryl-2-bromoacetamides (11a–11i) in an aprotic solvent. |