Synthesis, Docking Study and In-vitro Evaluation of Anti-Tuberculosis Activity of Tri Substituted Imidazoles Containing Quinoline Moiety
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A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.
Abstract
A simple, efficient, and cost-effective method has been employed for the synthesis of 2,4,5-trisubstituted imidazole derivatives (3a-j) containing quinoline substituent at 2nd position. Title compounds were obtained by multicomponent reaction (MCR), involving aryl substituted 1,2-diketone, quinoline carbaldehyde and ammonium acetate in the presence of acetic acid solvent under mild reaction conditions. The newly synthesized quinoline containing imidazole derivatives were confirmed through FT-IR, 1H-NMR, 13C-NMR and mass spectral analysis. In-vitro microplate alamar blue assay (MABA) to determine the MIC (minimum inhibitory concentration) values against Mycobacterium tuberculosis H37Rv was performed for the synthesized compounds. The synthesized compounds exhibited activity against Mycobacterium tuberculosis and among which compounds, 3d, 3f and 3i showed good activity. The highest activity was showed with compound 3i. The anti-mycobacterial activity results are well correlated with the computational molecular docking analysis, which was performed for the synthesized compounds prior to the evaluation of the activity.
참고문헌 (30)
- World Health Organization, "Treatment of Tuberculosis:Guidelines" (2010), WHO Press
- Espinal, M. A., , Tuberculosis, 83, pp.44~ (2003)
- Bhardwaj, N., , Curr. Tradit. Med, 7, pp.5~ (2021)
- Nasveld, P., , Trans. R. Soc. Trop. Med. Hyg, 99, pp.2~ (2005)
- Eswaran, S., , Eur. J. Med. Chem, 44, pp.4637~ (2009)
- Denny, W. A., "U.S Patent, 2006, 7064117", ~ (2006)
- Leatham, P., , Eur. J. Rheumatol. Inflamm, 6, pp.209~ (1983)
- Muruganantham, N., , Biol. Pharm. Bull, 27, pp.1683~ (2004)
- Maguire, M. P., , J. Med. Chem, 37, pp.2129~ (1994)
- Strekowski, L., , J. Med. Chem, 34, pp.1739~ (1991)
- Mahboub, B., "Tuberculosis: Current Issues in Diagnosis and Management", pp.1~480 (2013)
- Negi, A., , Biorg. Med. Chem, 23, pp.5654~ (2015)
- Mungra, D. C., , Med. Chem. Res, 20, pp.782~ (2011)
- Wen, S.-Q., , Bioorg. Med. Chem. Lett, 26, pp.2768~ (2016)
- Jourshari, M. S., , Chin. Chem. Lett, 24, pp.993~ (2013)
- Gangula, M. R., , Asian J. Chem, 5, pp.1216~ (2012)
- Wani, M. Y., , Biorg. Med. Chem, 23, pp.4172~ (2015)
- Gupta, P., , Eur. J. Med. Chem, 39, pp.805~ (2004)
- Desai, N., , Bioorg. Med. Chem. Lett, 26, pp.4030~ (2016)
- Siddiqui, S. A., , Tetrahedron Lett, 61, pp.3539~ (2005)
- Steck, E. A., , J. Am. Chem. Soc, 65, pp.452~ (1943)
- Shaabani, A., , J. Mol. Catal. A: Chem, 249, pp.246~ (2006)
- Sharma, S. D., , Tetrahedron Lett, 49, pp.2216~ (2008)
- Sangshetti, J. N., , J. Chem. Sci, 120, pp.463~ (2008)
- Heravi, M. M., , J. Mol. Catal. A: Chem, 263, pp.279~ (2007)
- Wolkenberg, S. E., , Org. Lett, 6, pp.1453~ (2004)
- Somashekara, B., , J. Chem. Sci, 131, pp.1~ (2019)
- Abdel-Wahab, B. F., , J. Chem, 2013, pp.1~ (2013)
- Collins, L., , Antimicrob. Agents Chemother, 41, pp.1004~ (1997)
- Krishna, V. S., , J. Comput. Aided Mol. Des, 33, pp.357~ (2019)