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Abstract
The analogs of nitrogen-based heterocycles occupy an exclusive position as a value of more than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. Among many N-containing heterocycles, quinolines have become important due to their variety of applications in medicinal, synthetic organic chemistry as well as in the field of industrial chemistry. Present work gives information about the green and clean synthesis using multicomponent reactions (MCRs) methods and L-proline and ammonium acetate as a catalyst for the synthesis of quinoline derivatives. Synthesized quinoline derivatives undergo spectroscopic analysis and their biological evaluation.
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References
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References
J.E. Anthony, Functionalized Acenes and Heteroacenes for Organic Electronics, Chem. Rev., 106, 5028 (2006); https://doi.org/10.1021/cr050966z
N.A. McGrath, M. Brichacek and J.T. Njardarson, A Graphical Journey of Innovative Organic Architectures That Have Improved Our Lives, J. Chem. Educ., 87, 1348 (2010); https://doi.org/10.1021/ed1003806
S. Kumar, S. Bawa and H. Gupta, Biological Activities of Quinoline Derivatives, Mini Rev. Med. Chem., 9, 1648 (2009); https://doi.org/10.2174/138955709791012247
N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
M.A. Barmade, P.R. Murumkar, M.K. Sharma and M.R. Yadav, Medicinal Chemistry Perspective of Fused Isoxazole Derivatives, Curr. Top. Med. Chem., 16, 2863 (2016); https://doi.org/10.2174/1568026616666160506145700
E. Vitaku, D.T. Smith and J.T. Njardarson, Analysis of the Structural Diversity, Substitution Patterns and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals, J. Med. Chem., 57, 10257 (2014); https://doi.org/10.1021/jm501100b
U. Desai, S. Mitragotri, T. Thopate, D. Pore and P. Wadgaonkar, A Highly Efficient Synthesis of Trisubstituted Quinolines using Sodium Hydrogensulfate on Silica Gel as a Reusable Catalyst, ARKIVOC, 15, 198 (2006); https://doi.org/10.3998/ark.5550190.0007.f24
E. Ebenso, K. Khaled, S. Shukla, A. Singh, N. Eddy, M. Saracoglu, F. Kandemirli, L.C. Murulana, A.K. Singh, S.K. Shukla, B. Hammouti, K.F. Khaled, M.A. Quraishi, I.B. Obot and N.O. Eddy, Quantum Chemical Investigations on Quinoline Derivatives as Effective Corrosion Inhibitors for Mild Steel in Acidic Medium, Int. J. Electrochem. Sci., 7, 5643 (2012).
M. Özyanik, S. Demirci, H. Bektas, N. Demirbas, A. Demirbas and S.A. Karaoglu, Preparation and Antimicrobial Activity Evaluation of Some Quinoline Derivatives Containing an Azole Nucleus, Turk. J. Chem., 36, 233 (2012); https://doi.org/10.3906/kim-1109-9
P.R. Graves, J.J. Kwiek, P. Fadden, R. Ray, K. Hardeman, A.M. Coley, M. Foley and T.A.J. Haystead, Discovery of Novel Targets of Quinoline Drugs in the Human Purine Binding Proteome, Mol. Pharmacol., 62, 1364 (2002); https://doi.org/10.1124/mol.62.6.1364
J. Yadav, S.P. Kumar, G. Kondaji, R.S. Rao and K. Nagaiah, A Novel L-Proline Catalyzed Biginelli Reaction: One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones under Solvent-Free Conditions, Chem. Lett., 33, 1168 (2004); https://doi.org/10.1246/cl.2004.1168
Z. Hajimahdi, R. Zabihollahi, M.R. Aghasadeghi, S.H. Ashtiani and A. Zarghi, Novel Quinolone-3-Carboxylic Acid Derivatives as Anti-HIV-1 Agents: Design, Synthesis, and Biological Activities, Med. Chem. Res., 25, 1861 (2016); https://doi.org/10.1007/s00044-016-1631-x
H.D. Isenberg, Essential Procedures For Clinical Microbiology, ASM Press: Washington, DC (1998).
A. Sharma and M.K. Shah, Synthesis¸ Characterization and Biological Activity of Schiff Bases Derived from 3-(4-Substituted)-1-phenyl-1H-pyrazole-4-carbaldehyde and o-Aminophenol, Chem. Sci. Trans., 2, 871 (2013); https://doi.org/10.7598/cst2013.522