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Synthesis, Characterization and Molecular Modeling of Pyrazole-Quinoline Hybrids as New Class of Antibacterial, Antimicrobial, Anticancer Agents and DFT Study
Corresponding Author(s) : Rajat Patel
Asian Journal of Chemistry,
Vol. 35 No. 4 (2023): Vol 35 Issue 4, 2023
Abstract
A new series of pyrazole-quinoline hybrids were synthesized by a base-catalyzed cyclocondensation reaction through one-pot multi-component reaction, based on molecular hybridization techniques. All the compounds 10a-x were examined for in vitro antibacterial and anticancer activities. Enzyme inhibitory activities were carried out against FabH and EGFR. From the studied compounds, most of the compounds showed effective antibacterial as well as anticancer activity against used strains and cancer cell lines, respectively. The most potent inhibitory activity was displayed by compound 10r against EGFR and by compound 10i against FabH. Spatial arrangement of the molecule and their HOMO-LUMO was studied and explained by DFT theory, to evaluate plane angle respective to the core and substitutions. Docking studies indicated that compound 10r was bound to the active pocket of EGFR with hydrogen bond and π-H interaction with minimum binding energy and compound 10i was bound to the active site of FabH with hydrogen bond and π-H interaction having minimum binding energy. Based on their substitutions, the hypothetical plane arising in the molecule and their twist angles were related with their activities against EGFR and FabH as well as antibacterial and anticancer activities.
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- M.M. Heravi and V. Zadsirjan, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
- N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
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References
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N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu and S.B. Jonnalagadda, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
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A. Ansari, A. Ali, M. Asif and S. Shamsuzzaman, New J. Chem., 41, 16 (2017); https://doi.org/10.1039/C6NJ03181A
G. Steinbach, P.M. Lynch, R.K.S. Phillips, M.H. Wallace, E. Hawk, G.B. Gordon, N. Wakabayashi, B. Saunders, Y. Shen, T. Fujimura, L.-K. Su, B. Levin, L. Godio, S. Patterson, M.A. Rodriguez-Bigas, S.L. Jester, K.L. King, M. Schumacher, J. Abbruzzese, R.N. DuBois, W.N. Hittelman, S. Zimmerman, J.W. Sherman and G. Kelloff, N. Engl. J. Med., 342, 1946 (2000); https://doi.org/10.1056/NEJM200006293422603
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G. Friedrich, T. Rose and K. Rissler, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 766, 295 (2002); https://doi.org/10.1016/S0378-4347(01)00514-X
C. Hampp, A.G. Hartzema and T.L. Kauf, Value Health, 11, 389 (2008); https://doi.org/10.1111/j.1524-4733.2007.00281.x
I.M. Spitz, B.H. Novis, R. Ebert, S. Trestian, D. LeRoith and W. Creutzfeldt, Metabolism, 31, 380 (1982); https://doi.org/10.1016/0026-0495(82)90114-7
D. Luttinger and D.J. Hlasta, Annu. Rep. Med. Chem., 22, 21 (1987); https://doi.org/10.1016/S0065-7743(08)61151-3
K. Tsutomu and N. Toshitaka, Neuropharmacology, 17, 249 (1978); https://doi.org/10.1016/0028-3908(78)90108-9
J. García-Lozano, J. Server-Carrió, E. Escrivà, J.-V. Folgado, C. Molla and L. Lezama, Polyhedron, 16, 939 (1997); https://doi.org/10.1016/S0277-5387(96)00346-4
J.Y. Lee, K.W. Jeong, S. Shin, J.U. Lee and Y. Kim, Bioorg. Med. Chem., 17, 5408 (2009); https://doi.org/10.1016/j.bmc.2009.06.059
E.J. Meuillet and E.G. Bremer, Pediatr. Neurosurg., 29, 1 (1998); https://doi.org/10.1159/000028677
F. Bernardi, I.G. Csizmadia and A. Mangini, Organic Sulfur Chemistry, Elsevier: Amsterdam, The Netherlands (1985).
E. Block, Block Copolymers – Overview and Critical Survey, In: Reactions of Organosulfur Compounds, Academic Press: New York (1978).
S. Patai and Z. Rappoport, The Chemistry of Organic Selenium and Tellurium Compounds, John Wiley & Sons: New York (1986).
M.D. McReynolds, J.M. Dougherty and P.R. Hanson, Chem. Rev., 104, 2239 (2004); https://doi.org/10.1021/cr020109k
D.J. Ager, Chem. Soc. Rev., 11, 493 (1982); https://doi.org/10.1039/cs9821100493
E.A. Ilardi, E. Vitaku and J.T. Njardarson, J. Med. Chem., 57, 2832 (2014); https://doi.org/10.1021/jm401375q
P. Sharma, R. Patel, R.R. Koshti, A. Vyas and C.B. Sangani, Asian J. Chem., 34, 3169 (2022); https://doi.org/10.14233/ajchem.2022.23981
L.F. Tietze and A. Steinmetz, Synlett, 667 (1996); https://doi.org/10.1055/s-1996-5548
C.J. Xu and Y.Q. Shi, J. Chem. Crystallogr., 41, 1816 (2011); https://doi.org/10.1007/s10870-011-0178-4
N.H. Sapariya, B.K. Vaghasiya, R.P. Thummar, R.D. Kamani, K.H. Patel, P. Thakor, S.S. Thakkar, A. Ray and D.K. Raval, New J. Chem., 41, 10686 (2017); https://doi.org/10.1039/C7NJ01962A
F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci., 8, e1327 (2017); https://doi.org/10.1002/wcms.1327
R. Kurtaran, S. Odabasioglu, A. Azizoglu, H. Kara and O. Atakol, Polyhedron, 26, 5069 (2007); https://doi.org/10.1016/j.poly.2007.07.021