design, synthesis and evaluation of antitubercular activity of novel dihydropyridine containing imidazolyl substituent
نویسندگان
چکیده
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.
منابع مشابه
Design, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent
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 (...
متن کاملDesign, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent
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 (...
متن کاملDesign, Synthesis and Evaluation of Antitubercular Activity of Novel Dihydropyridine Containing Imidazolyl Substituent
Recent studies have indicated that 1, 4-dihydropyridine-3, 5-dicarboxamide derivatives show 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 dicyclohexylcarbamoyl were substituted at C-3 and C-5 positions of the DHP ring. In addition, 4 (5)-chloro-2-methyl...
متن کاملDesign, Synthesis and Antitubercular Evaluation of Novel Series of Pyrazinecarboxamide Metal Complexes
The interest in the synthesis of metallic complexes of different drugs to make them moreefficient in biological environment of the human body is seen for the last few decades. Widerange of metal complexes are already used in clinical practice which encourages additionalresearch for innovating new metal based drugs, such as metal-mediated antibiotics, antiparasitic,antiviral, antibacterial, and ...
متن کاملDesign, Synthesis and Antitubercular Evaluation of Novel Series of Pyrazinecarboxamide Metal Complexes
The interest in the synthesis of metallic complexes of different drugs to make them moreefficient in biological environment of the human body is seen for the last few decades. Widerange of metal complexes are already used in clinical practice which encourages additionalresearch for innovating new metal based drugs, such as metal-mediated antibiotics, antiparasitic,antiviral, antibacterial, and ...
متن کاملSynthesis and Antitubercular Activity of N3,N5-Diaryl-4-(5-arylisoxazol-3-yl)-1,4-dihydropyridine-
5-Arylisoxazolyl-3-carboxaldehydes were condensed with N-aryl acetoaceta¬mide and ammonium acetate in methanol to give N3,N5-diaryl-4-(5-arylisoxazol-3-yl)-1,4-dihydropyridine-3,5-dicarboxamides. All compounds were screened for their antitubercular activity against Mycobacterium tuberculosis (H37Rv). The results for new synthesized compounds showed a moderate activity in comparison to rifampicin.
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عنوان ژورنال:
iranian journal of pharmaceutical researchجلد ۱۴، شماره ۴، صفحات ۱۰۶۷-۱۰۷۵
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