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Synthesis, Molecular Docking and Radical Scavenging Activity of 1,2,4,5-Tetrasubstituted Imidazole Derivatives
Corresponding Author(s) : Giriyapura R. Vijayakuma
Asian Journal of Chemistry,
Vol. 31 No. 11 (2019): Vol 31 Issue 11
Abstract
A series of 1,2,4,5-tetrasubstituted imidazoles (2a-g) were synthesized using 1,2-diketone, 1-naphthaldehyde, substituted aromatic amine and ammonium acetate in the presence of ceric ammonium nitrate as a catalyst. The synthesized compounds were characterized by FT-IR, 1H NMR, Mass spectra and explored for their antioxidant activity by DPPH free radical scavenging assay method. Among the synthesized compounds 2a, 2e and 2f exhibit good antioxidant activities. Molecular docking study was also been performed to know the possible interactions between the synthesized compound and antioxidant receptor 3MNG.
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References
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S. Naureen, F. Ijaz, M.A. Munawar, N. Asif, F. Chaudhry, M. Ashraf and M.A. Khan, J. Chil. Chem. Soc., 62, 3583 (2017); https://doi.org/10.4067/s0717-97072017000303583.
S.L. Gaonkar, K.M. Lokanatha Rai and N. Suchetha Shetty, Med. Chem. Res., 18, 221 (2009); https://doi.org/10.1007/s00044-008-9121-4.
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S.A. Laufer, D.R.J. Hauser, D.M. Domeyer, K. Kinkel and A.J. Liedtke, J. Med. Chem., 51, 4122 (2008); https://doi.org/10.1021/jm701529q.
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J. Safari, S. Gandomi-Ravandi and Z. Akbari, J. Adv. Res., 4, 509 (2013); https://doi.org/10.1016/j.jare.2012.09.001.
S.D. Sharma, P. Hazarika and D. Konwan, Tetrahedron Lett., 49, 2216 (2008); https://doi.org/10.1016/j.tetlet.2008.02.053.
M. Khoshneviszadeh and M. Mahdavi, ARKIVOC, 343 (2017); https://doi.org/10.24820/ark.5550190.p010.039.
V. Kumar, R. Mamgain and N. Singh, Res. J. Chem. Sci., 2, 18 (2012).
B.F. Mirjalili, A.H. Bamoniri and L. Zamani, Sci. Iran. C, 19, 565 (2012); https://doi.org/10.1016/j.scient.2011.12.013.
K. Nikoofar, M. Haghighi, M. Lashanizadegan and Z. Ahmadvand, J. Taibah Univ. Sci., 9, 570 (2015); https://doi.org/10.1016/j.jtusci.2014.12.007.
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G.M. Ziarani, A. Badiei, N. Lashgari and Z. Farahani, J. Saudi Chem. Soc., 20, 419 (2016); https://doi.org/10.1016/j.jscs.2013.01.005.
J. Safari, S. Naseh, Z. Zarnegar and Z. Akbari, J. Taibah Univ. Sci., 8, 323 (2014); https://doi.org/10.1016/j.jtusci.2014.01.007.
W. Li and Y. Lam, J. Comb. Chem., 7, 644 (2005); https://doi.org/10.1021/cc049818x.
A.P.G. Nikalje, M.S. Ghodke, F.A. Kalam Khan and J.N. Sangshetti, Chin. Chem. Lett., 26, 108 (2015); https://doi.org/10.1016/j.cclet.2014.10.020.
D.S. Raghuvamshi and K.N. Singh, Indian J. Chem., 49B, 1394 (2010).
Z.K. Jaberi and M. Barekat, Chin. Chem. Lett., 21, 1183 (2010); https://doi.org/10.1016/j.cclet.2010.06.012.
S. Samai, G.C. Nandi, P. Singh and M.S. Singh, Tetrahedron, 65, 10155 (2009); https://doi.org/10.1016/j.tet.2009.10.019.
K. Rajaguru, R. Suresh, A. Mariappan, S. Muthusubramanian and N. Bhuvanesh, Org. Lett., 16, 744 (2014); https://doi.org/10.1021/ol403456b.
Y.M. Ren and C. Cai, J. Chem. Res., 34, 133 (2010); https://doi.org/10.3184/030823410X12659021476402.
R.M. Shafeeulla, G. Krishnamurthy, H.S. Bhojyanaik and T. Manjuraj, J. Turkey Chem. Soc., 4A, 787 (2017); https://doi.org/10.18596/jotcsa.309261.
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