Issue

Vol. 29 No. 11 (2017): Vol 29 Issue 11

Copyright (c) 2017 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Design, Synthesis, Molecular Docking and Biological Evaluation of Novel Coumarin-Oxime Ether Derivatives as COX-2 Inhibitors

https://doi.org/10.14233/ajchem.2017.20865
M. Vijaya Bhargavi
RBVRR Women's College of Pharmacy, 3-4-343, Barkathpura, Hyderabad-500 027, India; Department of Pharmacy, Faculty of Technology, Osmania University, Hyderabad-500 007, India
P. Shashikala
Department of Pharmacy, Faculty of Technology, Osmania University, Hyderabad-500 007, India
M. Sumakanth
RBVRR Women's College of Pharmacy, 3-4-343, Barkathpura, Hyderabad-500 027, India
Shravan Kumar Gunda
Department of Pharmacy, Faculty of Technology, Osmania University, Hyderabad-500 007, India

Corresponding Author(s) : M. Vijaya Bhargavi

mvijayabhargavi@gmail.com

Asian Journal of Chemistry, Vol. 29 No. 11 (2017): Vol 29 Issue 11

Abstract

Coumarin-oxime ether derivatives (14-25) were synthesized by an efficient and straight forward procedure from the reaction of 3-acetyl coumarin (1) and o-substituted benzyl hydroxyl amines (2-13) in pyridinium p-toluenesulfonate/dichloromethane (PPTS/DCM) at reflux temperature. High yields and simple operations are important features of this methodology. The method is very useful for the construction of many biologically active oxime ether derivatives. The structures of the synthesized compounds are established based on IR, NMR and MASS spectrometry. Molecular docking studies were performed against selective COX-2 enzyme using Discovery Studio v3.5. The compounds with good LibDock score were screened for their in vivo anti-inflammatory activity by paw edema method, employing indomethacin as a reference standard.

Keywords

3-Acetyl coumarin Benzyl hydroxylamines Oxime ethers Docking COX-2
Bhargavi, M. V., Shashikala, P., Sumakanth, M., & Gunda, S. K. (2017). Design, Synthesis, Molecular Docking and Biological Evaluation of Novel Coumarin-Oxime Ether Derivatives as COX-2 Inhibitors. Asian Journal of Chemistry, 29(11), 2559–2564. https://doi.org/10.14233/ajchem.2017.20865
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. K.N. Venugopala, V. Rashmi and B. Odhav, BioMed Res. Int., Article ID 963248 (2013); http://dx.doi.org/10.1155/2013/963248.
  2. S. Sandhu, Y. Bansal, O. Silakari and G. Bansal, Bioorg. Med. Chem., 22, 3806 (2014); https://doi.org/10.1016/j.bmc.2014.05.032.
  3. G. Cravotto, G.M. Nano, G. Palmisano and S. Tagliapietra, Tetrahedron Asymm., 12, 707 (2001); https://doi.org/10.1016/S0957-4166(01)00124-0.
  4. L. Schio, F. Chatreaux and M. Klich, Tetrahedron Lett., 41, 1543 (2000); https://doi.org/10.1016/S0040-4039(99)02351-5.
  5. A. Lacy and O. Kennedy, Curr. Pharm. Des., 10, 3797 (2004); https://doi.org/10.2174/1381612043382693.
  6. A. Witaicenis, L.N. Seito, A. da Silveira Chagas, L.D. de Almeida, A.C. Luchini, P. Rodrigues-Orsi, S.H. Cestari and L.C. Di Stasi, Phytomedicine, 21, 240 (2014); https://doi.org/10.1016/j.phymed.2013.09.001.
  7. T.O. Olomola, R. Klein, N. Mautsa, Y. Sayed and P.T. Kaye, Bioorg. Med. Chem., 21, 1964 (2013); https://doi.org/10.1016/j.bmc.2013.01.025.
  8. P. Anand, B. Singh and N. Singh, Bioorg. Med. Chem., 20, 1175 (2012); https://doi.org/10.1016/j.bmc.2011.12.042.
  9. K. Venkata Sairam, B. M. Gurupadayya, R. S. Chandan, D. K. Nagesha and B. Vishwanathan, Curr. Drug Deliv., 13, 186 (2016); https://doi.org/10.2174/1567201812666150702102800.
  10. M. Khoobi, A. Foroumadi, S. Emami, M. Safavi, G. Dehghan, B.H. Alizadeh, A. Ramazani, A. Shafiee, Chem. Biol. Drug Des., 78, 580 (2011); https://doi.org/10.1111/j.1747-0285.2011.01175.x.
  11. J. Grover and S.M. Jachak, RSC Adv., 5, 38892 (2015); https://doi.org/10.1039/C5RA05643H.
  12. M. Babazadeh-Qazijahani, H. Badali, H. Irannejad, M.H. Afsarian and S. Emami, Eur. J. Med. Chem., 76, 264 (2014); https://doi.org/10.1016/j.ejmech.2014.02.019.
  13. S. Parthiban, V. Kabilan, V. Ramkumar and Y.T. Jeong, Bioorg. Med. Chem. Lett., 20, 6452 (2010); https://doi.org/10.1016/j.bmcl.2010.09.079.
  14. J.-H. Chern, C.-C. Lee, C.-S. Chang, Y.-C. Lee, C.-L. Tai, Y.-T. Lin, K.-S. Shia, C.-Y. Lee and S.-R. Shih, Bioorg. Med. Chem. Lett., 14, 5051 (2004); https://doi.org/10.1016/j.bmcl.2004.07.084.
  15. F. Delmas, M. Gasquet, P. Timon-David, N. Madadi, P. Vanelle, A. Vaille and J. Maldonado, Eur. J. Med. Chem., 28, 23 (1993); https://doi.org/10.1016/0223-5234(93)90075-P.
  16. S.M. El-Gamal, S.M. Bayomi, S.M. El-Ashry, S.A. Said, A.A.-M. Abdel-Aziz and N.I. Abdel-Aziz, Eur. J. Med. Chem., 45, 1403 (2010); https://doi.org/10.1016/j.ejmech.2009.12.041.
  17. M.R. Gannarapu, S.B. Vasamsetti, N. Punna, N.K. Royya, S.R. Pamulaparthy, J.B. Nanubolu, S. Kotamraju and N. Banda, Eur. J. Med. Chem., 75, 143 (2014); https://doi.org/10.1016/j.ejmech.2013.12.053.
  18. A. Emami, A. Kebriaeezadeh, N. Ahangar and R. Khorasani, Bioorg. Med. Chem. Lett., 21, 655 (2011); https://doi.org/10.1016/j.bmcl.2010.12.021.
  19. T. Chakravarti, T. Akhtar, B. Rai, M. Yadav, J. Akhtar Siddiqui, S.K. Dhar Dwivedi, R. Thakur, A.K. Singh, A.K. Singh, H. Kumar, K. Khan, S. Pal, S.K. Rath, J. Lal, R. Konwar, A.K. Trivedi, D. Datta, D.P. Mishra, M.M. Godbole, S. Sanyal, N. Chattopadhyay and A. Kumar, J. Med. Chem., 57, 8010 (2014); https://doi.org/10.1021/jm500873e.
  20. K. Park, K. Lee, S.-J. Park, B. Ahn, J.-C. Lee, H.Y. Cho and K.-I. Lee, Bioorg. Med. Chem. Lett., 15, 3307 (2005); https://doi.org/10.1016/j.bmcl.2005.03.082.
  21. Y.P. Luo, Q. Gong, Q. Chen, G.F. Yang, Chin. J. Org. Chem., 28, 1561 (2008).
  22. L.L. Jiang, C.N. Chen, Y.F. Zhou, Q. Chen, G.F. Yang, Chin. J. Org. Chem., 29, 1392 (2009).
  23. M. Dai, X. Fu, F. He, L. Jiang, Y. Li, F. Liang, L. Liu, Y. Mi, Y.-C. Xu, G. Xun, X. Yan, Z. Yu and J.Y. Zhang, Heterocyclic Oxime Compounds, WO 2011/020861A1 (2011).
  24. C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 1 Download : 0