Design, Synthesis and Anti-Tubercular Activity of Novel 1, 4-Dihydropyrine-3, 5-Dicarboxamide Containing 4(5)-Chloro-2-Ethyl-5(4)-Imidazolyl Moiety

Document Type: Research article

Authors

1 Chemical Injuries Research Center, Baqiyatallah University of Medical Sciences, Tehran, Iran.

2 Department of Medicinal Chemistry, Pharmaceutical Sciences branch, Islamic Azad University, Tehran, Iran

3 Department of Medicinal Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran.

4 Department of Bioinformatics and Drug design, Institute Pasteur, Tehran, Iran

5 Department of Bioinformatics and Drug design, Institute Pasteur, Tehran, Iran.

6 Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran.

Abstract

Current researches have showed that N3, N5-diaryl-2, 6-dimethyl -1, 4-dihydropyrine-3, 5- dicarboxamide analogues demonstrate notable anti-tubercular activity. In this study, Hantzsch condensation was used to design and synthesize new analogues of dihydropyridine (DHP). Different diary carboxamides were inserted at positions 3 and 5 of the DHP ring. 4(5)-chloro-2-ethyl-5(4)-imidazolyl moiety was considered at position 4 of the DHP ring. The structures of prepared ligands were characterized using TLC followed by FT-IR, elemental analysis, Mass and proton NMR. Results of anti-tubercular activity have indicated all the prepared ligands 3a-f inhibit the mycobacterium tuberculosis growth and the most potent compounds were 3c (3,4-Cl) and 3b (4-Cl). The in-vitro obtained data are agreement with our computational predictions in terms of partial atomic charge of carbonyl moieties at the positions 3 and 5 of dihydropyridine ring and the logP of the molecules.

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