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One-Pot Synthesis and Characterization of 3,4-Dihydropyrimidin-2(1H)-one Derivatives using Sulphonated Reduced Graphene Oxide Nanoparticles via Biginelli Cyclocondensation and its Cytotoxic Studies
Corresponding Author(s) : M. Bhaskara Rao
Asian Journal of Chemistry,
Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022
Abstract
A facile one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones (4a-h) was performed in the presence of sulphonated reduced graphene oxide nanoparticles (SrGO NPs), using various substituted aromatic aldehydes (1a-h), β-keto ester (2) and urea (3). Methanol solvent mediated the reaction, under refluxing conditions. The synthesized SrGO NPs were characterized using XRD, SEM-EDS and Raman spectroscopic methods. The structural moieties of the organic compounds were confirmed by 1H NMR, 13C NMR, FTIR and Mass spectroscopic techniques. The in vitro anticancer activity of the synthesized derivatives (4a-h) was investigated using MTT (4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) colorimetric assay as per American Type Culture Collection protocol. The cytotoxic studies were conducted against MCF-7, SKNSH human cells, using doxorubicin as the standard. Majority of the derivatives have exhibited superior anticancer activity.
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T. Shimatani, N. Hosotani, M. Ohnishi, K. Kumagai and I. Saji, J. Antibiot. (Tokyo), 59, 29 (2006); https://doi.org/10.1038/ja.2006.5
L. Ismaili, A. Nadaradjane, L. Nicod, C. Guyon, A. Xicluna, J.F. Robert and B. Refouvelet, J. Eur. Med.Chem., 43, 1270 (2008); https://doi.org/10.1016/j.ejmech.2007.07.012
P.R. Bernstein, B.C. Gomes, B.J. Kosmider, E.P. Vacek and J.C. Williams, J. Med. Chem., 38, 212 (1995); https://doi.org/10.1021/jm00001a028
P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893).
Z. Karimi-Jaberi and M.S. Moaddeli, Int. Scholarly Res. Net., 2012, 474626 (2012); https://doi.org/10.5402/2012/474626
S.P. Bahekar, P.B. Sarode, M.P. Wadekar and H.S. Chandak, J. Saudi Chem. Soc., 21, 415 (2017); https://doi.org/10.1016/j.jscs.2015.09.004
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D. Kumar, B.G. Mishra and V.S. Rao, Indian J. Chem., 45B, 2325 (2006).
B.G. Mishra, D. Kumar and V.S. Rao, Catal. Commun., 7, 457 (2006); https://doi.org/10.1016/j.catcom.2006.01.002
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M.A. Bigdeli, G. Gholami and E. Sheikhhosseini, Chin. Chem. Lett., 22, 903 (2011); https://doi.org/10.1016/j.cclet.2010.12.030
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A. Khaskel, P. Gogoi, P. Barman and B. Bandyopadhyay, RSC Adv., 4, 35559 (2014); https://doi.org/10.1039/C4RA05244G
J. Safari and S. Gandomi-Ravandi, J. Mol. Struct., 1065-1066, 241 (2014); https://doi.org/10.1016/j.molstruc.2014.02.035
S.R. Jetti, A. Bhatewara, T. Kadre and S. Jain, Chin. Chem. Lett., 25, 469 (2014); https://doi.org/10.1016/j.cclet.2013.12.022
F. Shirini, M. Abedini and R. Pourhasan-Kisomi, Chin. Chem. Lett., 25, 111 (2014); https://doi.org/10.1016/j.cclet.2013.09.005
A.R. Katritzky, C.W. Ress and E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II, Pergamon Press: Oxford (1996).
D. Ayres and J.D. Loike, Chemistry and Pharmacology of Natural Products, In: Lignans: Chemical, Biological and Clinical Properties, Cambridge University Press, Cambridge (1990).
T. Eicher and S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, Wiley-VCH: Weinheim, Germany, Ed.: 2 (2003)
M. Saleem, H.J. Kim, M.S. Ali and Y.S. Lee, Nat. Prod. Rep., 22, 696 (2005); https://doi.org/10.1039/b514045p
M. Brahmayya, S.Y. Suen and S.A. Dai, J. Taiwan Inst. Chem. Eng., 83, 174 (2018); https://doi.org/10.1016/j.jtice.2017.12.003
M. Litvic, I. Veèenaj, Z.M. Ladišic, M. Lovric, V. Vinkovic and M. Filipan-Litvic, Tetrahedron, 66, 3463 (2010); https://doi.org/10.1016/j.tet.2010.03.024
D. Da Silva, S. Fernandes, A. Sabino and A. Fatima, Tetrahedron Lett., 52, 6328 (2011); https://doi.org/10.1016/j.tetlet.2011.08.175
J. Mondal, T. Sen and A. Bhaumik, Dalton Trans., 41, 6173 (2012); https://doi.org/10.1039/c2dt30106g
M. Nasr-Esfahani, J. Hoseini and F. Mohammadi, Chin. J. Catal., 32, 1484 (2011); https://doi.org/10.1016/S1872-2067(10)60263-X