design, synthesis and evaluation of antitubercular activity of novel dihydropyridine containing imidazolyl substituent

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

golnoush dehqani 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.

abstract

recent studies have indicated that 1, 4-dihydropyridine-3, 5-dicarboxamidederivativesshow significant anti-tubercular activity. in this research, new derivatives of 1, 4-dihydropyridine were designed and synthesized using hantzsch condensation in which dicyclohexyl and different dicyclohexylcarbamoylwere substituted at c-3 and c-5 positions of the dhp ring.in addition, 4 (5)-chloro-2-methyl-5 (4)-imidazolylmoiety was substituted at c-4 position of dhp.the structure of synthetized compounds were characterized by tlc, ir, elemental analysis and proton nmr.based on the in-vitro screening data, all of the designed and synthetized compounds (3a-3g)showed agood ability to inhibit the mycobacterium tuberculosis growth in terms of mic. aromatic carboxamide containing compounds were more potent than cyclohexylderivative and the most potent compound was 3a (4-nitrophenyl derivative). the experimental data are in agreement with our computational predictions in terms of partial atomic charge of carbonyl moieties at the c-3 and c-5 positions of dhp ring and partition coefficient of the molecules.

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Journal title:
iranian journal of pharmaceutical research

جلد ۱۴، شماره ۴، صفحات ۱۰۶۷-۱۰۷۵

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