Iman, M., Davood, A., Dehqani, G., Lotfinia, M., Sardari, S., Azerang, P., Amini, M. (2015). Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent. Iranian Journal of Pharmaceutical Research, 14(4), 1067-1075.
Maryam Iman; Asghar Davood; Golnoush Dehqani; Mahboubeh Lotfinia; Soroush Sardari; Parisa Azerang; Mohsen Amini. "Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent". Iranian Journal of Pharmaceutical Research, 14, 4, 2015, 1067-1075.
Iman, M., Davood, A., Dehqani, G., Lotfinia, M., Sardari, S., Azerang, P., Amini, M. (2015). 'Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent', Iranian Journal of Pharmaceutical Research, 14(4), pp. 1067-1075.
Iman, M., Davood, A., Dehqani, G., Lotfinia, M., Sardari, S., Azerang, P., Amini, M. Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent. Iranian Journal of Pharmaceutical Research, 2015; 14(4): 1067-1075.
Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent
1Chemical Injuries Research Center, Baqiyatallah University of Medical Sciences, Tehran, Iran
2Department of Medicinal Chemistry, Pharmaceutical Sciences branch, Islamic Azad University, Tehran, Iran
3Department of Medicinal Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran.
4Department of Bioinformatics and Drug design, Institute Pasteur, Tehran, Iran
5Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, 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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