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Synthesis and Anticancer Activity of Novel Carbohydrazide and Carboxamide Derivatives of Pyridine Fused Heterocyclic Derivatives
Corresponding Author(s) : K. Bhaskar
Asian Journal of Chemistry,
Vol. 34 No. 10 (2022): Vol 34 Issue 10, 2022
Abstract
A series of novel carbohydrazide and carboxamide derivatives of hetero-fused pyridine derivatives were synthesized starting from bis-trifluoromethyl containing pyridine 1. Compound 1 on Smiles rearrangement obtained compound 2, then compound 2 on coupling with diethyl ethoxymethylenemalonate (EMME), further reaction with POCl3 and hydrazine hydrate to obtain pyridopyrimidine hydrazide derivatives. This hydrazide derivative reacts with different substituted aromatic aldehydes to produce title carbohydrazide derivatives 6a-h. Pyridopyrimidine carboxylate compound on reaction with aliphatic amine to obtain carboxamide derivatives 7a-e. All the final products evaluated for their anticancer activity, against four human cancer cell lines and promising compounds have been identified. Compounds 7a and 7b exhibits remarkable activity.
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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
M.M. Heravi and V. Zadsirjan, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
R.F. Costa, L.C. Turones, K.V.N. Cavalcante, I.A. Rosa Jr., C.H. Xavier, L.P. Rosseto, H.B. Napolitano, P.F. de S. Castro, M.L.F. Neto, G.M. Galvão, R. Menegatti, G.R. Pedrino, E.A. Costa, J.L.R. Martins and J.O. Fajemiroye, Front. Pharmacol., 12, 666725 (2021); https://doi.org/10.3389/fphar.2021.666725
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L.P. Singh, Syst. Rev. Pharm., 13, 410 (2022); https://doi.org/10.31858/0975-8453.13.4.410-413
A. Jemal, R. Siegel, E. Ward, T. Murray, J. Xu and M.J. Thun, Cancer J. Clin., 57, 43 (2007); https://doi.org/10.3322/canjclin.57.1.43
E.M. Mohi El-Deen, M.M. Anwar, A.A.A. El-Gwaad, E.A. Karam, M.K. El-Ashrey and R.R. Kassab, Molecules, 27, 803 (2022); https://doi.org/10.3390/molecules27030803
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J. Ram, D.A. Vanden Berghe and A.J.J. Vlietinck, Heterocycl. Chem., 25, 217 (1988); https://doi.org/10.1002/jhet.5570250133
J.R. Piper, G.S. McCaleb, J.A. Montgomery, R.L. Kisliuk, Y. Gaumont and F.M. Sirotnak, J. Med. Chem., 29, 1080 (1986); https://doi.org/10.1021/jm00156a029
R.K. Robins and G.H.J. Hitchings, J. Am. Chem. Soc., 80, 3449 (1958); https://doi.org/10.1021/ja01546a061
H. M. F. Madkour, H. M. F. Madkour, M. A. I. Salem, T. M. AbdelRahman and M. E. Azab, Heterocycles, 38, 57 (1994); https://doi.org/10.3987/COM-91-5873
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C. Isanbor and D. O’Hagan, J. Fluor. Chem., 127, 303 (2006); https://doi.org/10.1016/j.jfluchem.2006.01.011
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