Synthesis of Novel 3-(4-tert-Butylphenyl)-5-Cylopropyl-4H-1,2,4-Triazole Derivatives with Antioxidative and Antimicrobial Activities

Abstract

Background: In this work, new heterocyclic compounds containing 3-(4-tertbutylphenyl)- 5-cyclopropyl-4H-1,2,4-triazole ring were synthesized, starting from iminoester hydrochlorides and 4-tert-butylbenzhyrazide. Methods: Ethyl N-[(4-tert-butylphenyl)carbonyl]cyclopropanecarbohydrazonoate was used to synthesize 4-amino-3-(4-tert-butylphenyl)-5-cyclopropyl-4H-1,2,4-triazole, 3-(4-tert-butylphenyl)-5- cyclopropyl-4-(arylmethyleneamino)-4H-1,2,4-triazole, 3-(4-tert-butylphenyl)-5-cyclopropyl-4- (arylmethylamino)-4H-1,2,4-triazole and their phthalonitrile derivatives sequentially. Results: Seventeen new 3-(4-tert-butylphenyl)-5-cyclopropyl-4H-1,2,4-triazole derivatives were synthesized and their antioxidant and antimicrobial activities were determined. Conclusion: Imine and amine derivatives were better antioxidants than phthalonitrile derivatives. Doubly fluorination compounds appeared to result in higher activity. The compounds tested with five microorganisms showed better activity against B. subtilis with the antimicrobial activity of two far exceeding that of ampicillin. Imine and amine derivatives were better antimicrobials than phthalonitrile derivatives.