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Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020

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Isoxazoles-A Biocompatible Radical Scavenging Agents: Citrus Juice Mediated Environmentally Benign Synthesis and Characterization

https://doi.org/10.14233/ajchem.2020.22871
K.R. Raghavendra
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru-570005, India ; Department of Chemistry, S.B.R.R. Mahajana College, Mysuru-570012, India
M.G. Prabhudeva
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru-570005, India ; Department of Chemistry, S.B.R.R. Mahajana College, Mysuru-570012, India
A. Dileep Kumar
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru-570005, India
K. Ajay Kumar
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru-570005, India
H.P. Jayadevappa
Department of Chemistry, Yuvaraja College, University of Mysore, Mysuru-570005, India

Corresponding Author(s) : H.P. Jayadevappa

hpjayadevappa@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 12 (2020): Vol 32 Issue 12, 2020

Abstract

This study demonstrates the efficient eco-friendly synthesis of a series of isoxazole derivatives 5a-h through (3+2) annulation of chalcones 3a-h and hydroxylamine (4) in citrus juice medium. The synthesized compounds were characterized by spectroscopic and CHN analysis, and assessed in vitro for their antioxidant susceptibilities by DPPH and hydroxyl radical scavenging assays. The result shows that compounds 5a, 5b, 5d and 5h have excellent DPPH and hydroxyl radical scavenging activity in both assays and therefore these molecule could serve as potent antioxidant agents.

Keywords

Isoxazoles Citrus juice Hydroxylamine Annulation Antioxidant Chalcone Cyclocondensation
Raghavendra, K., Prabhudeva, M., Dileep Kumar, A., Ajay Kumar, K., & Jayadevappa, H. (2020). Isoxazoles-A Biocompatible Radical Scavenging Agents: Citrus Juice Mediated Environmentally Benign Synthesis and Characterization. Asian Journal of Chemistry, 32(12), 2997–3001. https://doi.org/10.14233/ajchem.2020.22871
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References
  1. S.M. Gomha, M.A. Abdallah, I.M. Abbas and M.S.H. Kazem, Med. Chem., 14, 344 (2018); https://doi.org/10.2174/1573406413666171020114105
  2. S.L. Gaonkar and U.N. Vignesh, Res. Chem. Intermed., 43, 6043 (2017); https://doi.org/10.1007/s11164-017-2977-5
  3. H.V. Chavan, L.K. Adsul, A.S. Kotmale, V.D. Dhakane, V.N. Thakare and B.P. Bandgar, J. Enzym. Inhib. Med. Chem., 30, 22 (2015); https://doi.org/10.3109/14756366.2013.873037
  4. S. Kumari, S.K. Paliwal and R. Chauhan, Curr. Bioact. Comp., 14, 39 (2018); https://doi.org/10.2174/1573407212666161101152735
  5. B. Caliskan, E. Sinoplu, K. Ibis, E.A. Guzelcan, R.C. Ataly and E. Banoglu, J. Enzyme Inhib. Med. Chem., 33, 1352 (2018); https://doi.org/10.1080/14756366.2018.1504041
  6. I. Filali, A. Romdhane, M. Znati, H.B. Jannet and J. Bouajila, Med. Chem., 12, 184 (2016); https://doi.org/10.2174/157340641202160209104115
  7. B.C. Manjunath, M. Manjula, K.R. Raghavendra, S. Shashikanth, K.A. Kumar and N.K.L. Rai, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o121 (2014); https://doi.org/10.1107/S1600536813034612
  8. K.R. Raghavendra, K.A. Kumar and S. Shashikanth, Int. J. Pharm. Pharm. Sci., 6, 90 (2014).
  9. K.S. Kadam, T. Gandhi, A. Gupte, A.K. Gangopadhyay and R. Sharma, Synthesis, 48, 3996 (2016); https://doi.org/10.1055/s-0035-1561464
  10. L. Johnson, J. Powers, F. Ma, K. Jendza, B. Wang, E. Meredith and N. Mainolfi, Synthesis, 45, 171 (2013); https://doi.org/10.1055/s-0032-1317935
  11. P.V. Khairnar, T.-H. Lung, Y.-J. Lin, C.-Y. Wu, S.R. Koppolu, A. Edukondalu, P. Karanam and W. Lin, Org. Lett., 21, 4219 (2019); https://doi.org/10.1021/acs.orglett.9b01395
  12. K.A. Kumar, Int. J. ChemTech Res., 5, 3032 (2013).
  13. K.B. Umesha, K.A. Kumar and K.M.L. Rai, Synth. Commun., 32, 1841 (2002); https://doi.org/10.1081/SCC-120004066
  14. K.A. Kumar, K.M.L. Rai, K.B. Umesha and K.R. Prasad, Indian J. Chem., 40B, 269 (2001).
  15. K.A. Kumar, M. Govindaraju and G.V. Kumar, Indian J. Heterocycl. Chem., 20, 183 (2010).
  16. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B.Sharpless and V.V. Fokin, J. Am. Chem. Soc., 127, 210 (2005); https://doi.org/10.1021/ja0471525
  17. K.N. Tu, J.J. Hirner and S.A. Blum, Org. Lett., 18, 480 (2016); https://doi.org/10.1021/acs.orglett.5b03530
  18. Y. Ning, Y. Otani and T. Ohwada, J. Org. Chem., 83, 203 (2018); https://doi.org/10.1021/acs.joc.7b02573
  19. Z. Lai, Z. Li, Y. Liu, P. Yang, X. Fang, W. Zhang, B. Liu, H. Chang, H. Xu and Y. Xu, J. Org. Chem., 83, 145 (2018); https://doi.org/10.1021/acs.joc.7b02483
  20. E. Kobayashi and H. Togo, Synthesis, 51, 3723 (2019); https://doi.org/10.1055/s-0039-1690102
  21. X.-W. Zhang, W.-L. Hu, S. Chen and X.-G. Hu, Org. Lett., 20, 860 (2018); https://doi.org/10.1021/acs.orglett.7b04028
  22. L. Chen and S. Cui, J. Org. Chem., 84, 12157 (2019); https://doi.org/10.1021/acs.joc.9b01430
  23. C. Li, J. Li, F. Zhou, C. Li and W. Wu, J. Org. Chem., 84, 11958 (2019); https://doi.org/10.1021/acs.joc.9b01593
  24. P. Dai, X. Tan, Q. Luo, X. Yu, S. Zhang, F. Liu and W.-H. Zhang, Org. Lett., 21, 5096 (2019); https://doi.org/10.1021/acs.orglett.9b01683
  25. Y. Jeong, B.-I Kim, J. K. Lee and J.-S. Ryu, J. Org. Chem., 79, 6444 (2014); https://doi.org/10.1021/jo5008702
  26. Y. Shang, M. Hu, X. He, Z. Niu, Z. Yan and F. Zhou, Synthesis, 46, 510 (2014); https://doi.org/10.1055/s-0033-1340470
  27. Q.-F. Jia, P.M.S. Benjamin, J. Huang, Z. Du, X. Zheng, K. Zhang, A.H. Conney and J. Wang, Synlett, 24, 79 (2013); https://doi.org/10.1055/s-0032-1317923
  28. D.M. Lokeshwari and K.A. Kumar, Asian J. Chem., 29, 2660 (2017); https://doi.org/10.14233/ajchem.2017.20781
  29. R. Harigae, K. Moriyama and H. Togo, J. Org. Chem., 79, 2049 (2014); https://doi.org/10.1021/jo4027116
  30. W.S. El-Hamouly, A.-M.A. El-Khamry and E.M.H. Abbas, Indian J. Chem., 45B, 2091 (2006).
  31. S.K. Sahu, M. Banerjee, D. Sahu, C.C. Behera, G.C. Pradhan and M.A. Azam, Dhaka Univ. J. Pharm. Sci., 7, 113 (1970); https://doi.org/10.3329/dujps.v7i2.2165
  32. K.A. Kumar, K.M.L. Rai and K.B. Umesha, J. Chem. Res. (S), 436 (2001); https://doi.org/10.3184/030823401103168389
  33. G.V. Kumar, B.B.A. Khatoon, B.N. Mylarappa and K.A. Kumar, J. Chem. Pharm. Res., 7, 1293 (2015).
  34. Ch.V.N. Reddy, S. Raju, R.M. Nagi and E. Rajanarendar, Indian J. Chem., 49B, 1667 (2010).
  35. A.R. Parikh, N.A. Vekariya and M.D. Khunt, Indian J. Chem., 42B, 421 (2003).
  36. S.S. Panda, P.V.R. Chowdary and B.S. Jayashree, Indian J. Pharm. Sci., 71, 684 (2009); https://doi.org/10.4103/0250-474X.59554
  37. Rakesh, D. Bruhn, D.B. Madhura, M. Maddox, R.B. Lee, A. Trivedi, L. Yang, M.S. Scherman, J.C. Gilliland, V. Gruppo, M.R. McNeil, A.J. Lenaerts, B. Meibohm and R.E. Lee, Bioorg. Med. Chem., 20, 6063 (2012); https://doi.org/10.1016/j.bmc.2012.08.023
  38. S.Y. Hassan, Molecules, 18, 2683 (2013); https://doi.org/10.3390/molecules18032683
  39. J.G. Eugenio, L.C.O. Tatiane, M.A. Severino, R. Alessandra, D.L. Alessandro and H.M.G. Rosa, Braz. Dent. J., 23,22 (2012); https://doi.org/10.1590/S0103-64402012000100004
  40. B. Halliwell and J.M.C. Gutteridge, Free Radicals in Biology and Medicine: Clarendon Press, vol. 3, pp. 617-783 (1989).
  41. Shyam, D.M. Lokeshwari, K.A. Kumar and H.P. Jayadevappa, Int. J. ChemTech Res., 10, 9 (2017).
  42. N. Shivalingegowda, K. Kumara, D.K. Achutha, A.K. Kariyappa and L.N. Krishnappagowda, Chem. Data Coll., 15-16, 89 (2018); https://doi.org/10.1016/j.cdc.2018.04.006
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