Copyright (c) 2025 BHAMUNI M. R. , JAYAPRADHA S. R.

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Green Synthesis of Naphthyridine Derivatives and their Cytochrome Activity against Human Microsomal P450 1A2: Comparative Studies on Organic and Aqueous Media
Corresponding Author(s) : S.R. Jayapradha
Asian Journal of Chemistry,
Vol. 37 No. 8 (2025): Vol 37 Issue 8, 2025
Abstract
In this work, the synthetic protocol of naphthyridine derivatives through one pot reaction using aqueous and organic solvents are reported. The cascade reaction of malononitrile dimer and aldehyde leads to the formation of 5,7-diamino-2-(dicyanomethyl)-4-(4-oxobutyl)-1,2,3,4-tetrahydro-1,6-naphthyridine-3,8-dicarbonitrile (3) in organic solvents in moderate yield. But the study shows the attractive features of using like elixir solvent ‘water’ as green solvent and ionic liquid as a catalyst to reduce chemical usage and environmentally malignant formation. The present investigation highlights to synthesize naphthyridine derivative 3 in a good yield using aqueous solvent in comparison to organic solvents because green solvents are highly eco-friendly approach, low cost and simple methodology. The structure of naphthyridine derivative 3 using water/catalyst was confirmed by spectral techniques, there are no changes with the spectral studies which were carried out in organic solvents but the yield was more in aqueous media when compared with naphthyridine derivatives in an organic solvent. The newly synthesized naphthyridine compound were evaluated for their cytochrome activity against Human Microsomal P450 1A2 enzyme, the results of molecular docking reveals that the compound perhaps chosen as clinical drug.
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- I.N. Bardasov, A.U. Alekseeva, V.A. Tafeenko and O.V. Ershov, Synth. Commun., 49, 3343 (2019); https://doi.org/10.1080/00397911.2019.1665184
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References
I.N. Bardasov, A.U. Alekseeva, V.A. Tafeenko and O.V. Ershov, Synth. Commun., 49, 3343 (2019); https://doi.org/10.1080/00397911.2019.1665184
T. Devadoss, V. Sowmya and R. Bastati, ChemistrySelect, 6, 3610 (2021); https://doi.org/10.1002/slct.202004462
S.K. Srivastava, A. Jha, S.K. Agarwal, R. Mukherjee and A.C. Burman, Anticancer. Agents Med. Chem., 7, 685 (2007); https://doi.org/10.2174/187152007784111313
S.S. Choudhury, S. Jena, D.K. Sahoo, S. Shekh, R.K. Kar, A. Dhakad, K.H. Gowd and H.S. Biswal, ACS Omega, 6, 19304 (2021); https://doi.org/10.1021/acsomega.1c02798
E. Mohamed, A. Abdelmajeid, M. Behalo, A. Abel-Maaboud and K. Hebaish, Egypt. J. Chem., 65, 651 (2022); https://doi.org/10.21608/ejchem.2021.95621.4488
R.A. Carboni, D.D. Coffman and E.G. Howard, J. Am. Chem. Soc., 80, 2838 (1958); https://doi.org/10.1021/ja01544a061
V.V. Dotsenko, S.G. Krivokolysko and A.M. Semenova, Chem. Heterocycl. Compd., 54, 989 (2018); https://doi.org/10.1007/s10593-018-2383-y
A. Ashraf, Z. Shafiq, K. Mahmood, M. Yaqub and W. Rauf, RSC Adv., 10, 5938 (2020); https://doi.org/10.1039/C9RA09148C
S. Banoth, S. Perugu and S. Boda, J. Heterocycl. Chem., 55, 709 (2018); https://doi.org/10.1002/jhet.3092
B.B. Feng, M.M. Zhang and X.S. Wang, Polycycl. Aromat. Compd., 36, 478 (2016); https://doi.org/10.1080/10406638.2015.1014969
E.C. Taylor and K.S. Hartke, J. Am. Chem. Soc., 81, 2452 (1959); https://doi.org/10.1021/ja01519a044
F.M. Abdelrazek, N.A.L. Kassab, N.H. Metwally and N.A. Sobhy, Eur. J. Chem., 1, 368 (2010); https://doi.org/10.5155/eurjchem.1.4.368-372.104
B. Sonyanaik, D. Ravi, P. Shyam and K. Kishore, Research Square, 2023, 1, 1-14; https://doi.org/10.21203/rs.3.rs-2453479/v1
A.F. Eweas, N.M. Khalifa, N.S. Ismail, M.A. Al-Omar and A.M.M. Soliman, Med. Chem. Res., 23, 76 (2014); https://doi.org/10.1007/s00044-013-0604-6
E.P. Gallagher, K.L. Kunze, P.L. Stapleton and D.L. Eaton, Toxicol. Appl. Pharmacol., 141, 595 (1996); https://doi.org/10.1006/taap.1996.0326
K.A. Usmani, T.M. Cho, R.L. Rose and E. Hodgson, Drug Metab. Dispos., 34, 1606 (2006); https://doi.org/10.1124/dmd.106.010439
E.P. Gallagher, L.C. Wienkers, P.L. Stapleton, K.L. Kunze and D.L. Eaton, Cancer Res., 54, 101 (1994).
S. Sansen, J.K. Yano, R.L. Reynald, G.A. Schoch, K.J. Griffin, C.D. Stout and E.F. Johnson, J. Biol. Chem., 282, 14348 (2007); https://doi.org/10.1074/jbc.M611692200
A.A. Walsh, G.D. Szklarz and E.E. Scatt, Metabolism, 288, 12932 (2023).