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Synthesis, Characterization, Biological Evaluation and Molecular Docking Studies of Some Oxazinyl-Thiazolidinone Derivatives
Corresponding Author(s) : Ramarajan Rajalakshmi
Asian Journal of Chemistry,
Vol. 32 No. 9 (2020): Vol 32 Issue 9, 2020
Abstract
A series of new 4-thiazolidinone derivatives of 2-(4-chlorophenyl)-3-(6-(thiophen-2-yl)-4-p-tolyl-4H-1,3-oxazin-2-yl)-thiazolidin-4-one (7h-m) are synthesized because of its wide range of biological activities. 1H & 13C NMR, IR studies were applied for the elucidation of all the synthesized compounds. All the synthesized compounds have been tested for antidiabetic and antioxidant activity in vitro method against standard. The analogs 7h-m was evaluated for α-amylase and α-glucosidase inhibitory potential. The structures of all the compounds have been screened for antioxidant activity using DPPH radical scavenging assay, NO scavenging method. Molecular docking studies were accomplished in addition to understand the binding affinity of those compounds with PDBID 2HR7 which showed that the synthesized derivatives bind in the lively binding site of the target protein.
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- S. Kaur Manjal, R. Kaur, R. Bhatia, K. Kumar, V. Singh, R. Shankar, R. Kaur and R.K. Rawal, Bioorg. Chem., 75, 406 (2017); https://doi.org/10.1016/j.bioorg.2017.10.014
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References
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J. Blanchet and J. Zhu, Tetrahedron Lett., 45, 4449 (2004); https://doi.org/10.1016/j.tetlet.2004.04.055
D. Kaminskyy, D. Khyluk, O. Vasylenko and R. Lesyk, Tetrahedron Lett., 53, 557 (2012); https://doi.org/10.1016/j.tetlet.2011.11.095
A. Deep, S. Jain, P.C. Sharma, P. Phogat and M. Malhotra, Med. Chem. Res., 21, 1652 (2012); https://doi.org/10.1007/s00044-011-9679-0
A.A. Geronikaki, E.P. Pitta and K.S. Liaras, Curr. Med. Chem., 20, 4460 (2013); https://doi.org/10.2174/09298673113209990143
D. Havrylyuk, L. Mosula, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, Eur. J. Med. Chem., 45, 5012 (2010); https://doi.org/10.1016/j.ejmech.2010.08.008
M.S. El-Gaby, G.A. El-Hag Ali, A.A. El-Maghraby, M.T.A. El-Rahman and M.H. Helal, Eur. J. Med. Chem., 44, 4148 (2009); https://doi.org/10.1016/j.ejmech.2009.05.005
S.D. Firke, B.M. Firake, R.Y. Chauhari and V.R. Patil, Asian J. Res. Chem, 2, 157 (2009).
V.S. Palekar, A.J. Damle and S.R. Shukla, Eur. J. Med. Chem., 44, 5112 (2009); https://doi.org/10.1016/j.ejmech.2009.07.023
M. Haroun, C. Tratrat, K. Kositzi, E. Tsolaki, A. Petrou, B. Aldhubiab, M. Attimarad, S. Harsha, A. Geronikaki, K.N. Venugopala, H.S. Elsewedy, M. Sokovic, J. Glamoclija and A. Ciric, Curr. Top. Med. Chem., 18, 75 (2018); https://doi.org/10.2174/1568026618666180206101814
A. Deep, B. Narasimhan, S.M. Lim, K. Ramasamy, R.K. Mishra and V. Mani, RSC Adv., 6, 109485 (2016); https://doi.org/10.1039/C6RA23006G
S.G. Patil, R.R. Bagul, M.S. Swami, N. Kotharkar and K. Darade, Chin. Chem. Lett., 22, 883 (2011); https://doi.org/10.1016/j.cclet.2011.03.002
K.R.A. Abdellatif, M.A. Abdelgawad, H.A.H. Elshemy and S.S.R. Alsayed, Bioorg. Chem., 64, 1 (2016); https://doi.org/10.1016/j.bioorg.2015.11.001
G.N. Tageldin, S.M. Fahmy, H.M. Ashour, M.A. Khalil, R.A. Nassra and I.M. Labouta, Bioorg. Chem., 80, 164 (2018); https://doi.org/10.1016/j.bioorg.2019.03.018
O.S. Afifi, O.G. Shaaban, H.A.A. El Razik, S. El-Dine A. Shams ElDine, F.A. Ashour, A.A. El-Tombary and M.M. Abu-Serie, Bioorg. Chem., 87, 821 (2019); https://doi.org/10.1016/j.bioorg.2019.03.076
M.F. Ansari, D. Idrees, M.I. Hassan, K. Ahmad, F. Avecilla and A. Azam, Eur. J. Med. Chem., 144, 544 (2018); https://doi.org/10.1016/j.ejmech.2017.12.049
R. Ottanà, R. Maccari, M. Giglio, A. Del Corso, M. Cappiello, U. Mura, S. Cosconati, L. Marinelli, E. Novellino, S. Sartini, C. La Motta and F. Da Settimo, Eur. J. Med. Chem., 46, 2797 (2011); https://doi.org/10.1016/j.ejmech.2011.03.068
S. Rammohan, A.M. Zaini and S. Amirin, Acta Biochim. Polon., 55, 391 (2008).
M. Telagari and K. Hullatti, Indian J. Pharmacol., 47, 425 (2015); https://doi.org/10.4103/0253-7613.161270
L. Marcocci, J.J. Maguire, M.T. Droy-Lefaix and L. Packer, Biochem. Biophys. Res. Commun., 201, 748 (1994); https://doi.org/10.1006/bbrc.1994.1764
Schrodinger, version 9.0, Schrodinger, LLC, New York (2009).