design, synthesis and anti-tubercular activity of novel 1, 4-dihydropyrine-3, 5-dicarboxamide containing 4(5)-chloro-2-ethyl-5(4)-imidazolyl moiety

Authors

maryam iman chemical injuries research center, baqiyatallah university of medical sciences, tehran, iran.

asghar davood department of medicinal chemistry, pharmaceutical sciences branch, islamic azad university, tehran, iran

mahboubeh lotfinia department of medicinal chemistry, pharmaceutical sciences branch, islamic azad university, tehran, iran.

golnoush dehqani department of medicinal chemistry, pharmaceutical sciences branch, islamic azad university, 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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Journal title:
iranian journal of pharmaceutical research

جلد ۱۵، شماره ۴، صفحات ۷۹۱-۷۹۹

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