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Synthesis, Antioxidant Activity and DFT Study of Some Novel N-Methylated Indole Incorporating Isoxazole Moieties
Corresponding Author(s) : T.F. Abbs Fen Reji
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
A novel series of indolyl isoxazole derivatives were synthesized and the structure of the products is confirmed on the basis of IR, 1H NMR, MS and analytical data. The synthesized compounds were evaluated for their antioxidant and anticancer activities. The results revealed clearly those compounds 4b and 4d exhibited better radical scavenging ability. The optimized structural parameters of all compounds was carried out at the B3LYP/6-311++G (d, p) level of DFT basis set implemented in Gaussian 09 program package. Theoretical calculation of the title compounds were carried out using density functional theory method (DFT).
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- D.-H. He, Y.-C. Zhu, Z.-R. Yang and A.-X. Hu, J. Chin. Chem. Soc., 56, 268 (2009); https://doi.org/10.1002/jccs.200900039.
- W.R. Tully, C.R. Gardner, R.J. Gillespie and R. Westwood, J. Med. Chem., 34, 2060 (1991); https://doi.org/10.1021/jm00111a021.
- R. Gudipati, R.N. Reddy Anreddy and S. Manda, J. Enzyme Inhib. Med. Chem., 26, 813 (2011); https://doi.org/10.3109/14756366.2011.556630.
- P. Saluja, J.M. Khurana, K. Nikhil and P. Roy, RSC Adv., 4, 34594 (2014); https://doi.org/10.1039/C4RA02917H.
- V. Misik, K. Ondrias and A. Stasko, Life Sci., 65, 1879 (1999); https://doi.org/10.1016/S0024-3205(99)00441-5.
- M.A. Barmade, P.R. Murumkar, M.K. Sharma and M.R. Yadav, Curr. Top. Med. Chem., 16, 2863 (2016); https://doi.org/10.2174/1568026616666160506145700.
- W.M. El-Husseiny, M.A-A. El-Sayed, N.I. Abdel-Aziz, A.S. El-Azab, E.R. Ahmed and A.A.-M. Abdel-Aziz, J. Enzyme Inhib. Med. Chem., 33, 507 (2018); https://doi.org/10.1080/14756366.2018.1434519.
- W.S. Hamama, M.E. Ibrahim, A.A. Gooda and H.H. Zoorob, J. Heterocycl. Chem., 55, 2623 (2018); https://doi.org/10.1002/jhet.3322.
- H. Brahmbhatt, M. Molnar and V. Pavic, Karbala Int. J. Modern Sci., 4, 200 (2018); https://doi.org/10.1016/j.kijoms.2018.01.006.
- J. Wang, H. Tang, B. Hou, P. Zhang, Q. Wang, B.-L. Zhang, Y.-W. Huang, Y. Wang, Z.-M. Xiang, C.-T. Zi, X.-J. Wang and J. Sheng, RSC Adv., 7, 54136 (2017); https://doi.org/10.1039/C7RA11496F.
- A. Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009); https://doi.org/10.1016/j.ejmech.2009.06.024.
- M. Prabhaharan, A.R. Prabakaran, S. Gunasekaran and S. Srinivasan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 123, 392 (2014); https://doi.org/10.1016/j.saa.2013.12.056.
- J.B. Foresman and M. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, edn 2 (1996).
- W.S. Hamama, M.A. Gouda, M.H. Badr and H.H. Zoorob, Med. Chem. Res., 22, 3556 (2013); https://doi.org/10.1007/s00044-012-0336-z.
References
D.-H. He, Y.-C. Zhu, Z.-R. Yang and A.-X. Hu, J. Chin. Chem. Soc., 56, 268 (2009); https://doi.org/10.1002/jccs.200900039.
W.R. Tully, C.R. Gardner, R.J. Gillespie and R. Westwood, J. Med. Chem., 34, 2060 (1991); https://doi.org/10.1021/jm00111a021.
R. Gudipati, R.N. Reddy Anreddy and S. Manda, J. Enzyme Inhib. Med. Chem., 26, 813 (2011); https://doi.org/10.3109/14756366.2011.556630.
P. Saluja, J.M. Khurana, K. Nikhil and P. Roy, RSC Adv., 4, 34594 (2014); https://doi.org/10.1039/C4RA02917H.
V. Misik, K. Ondrias and A. Stasko, Life Sci., 65, 1879 (1999); https://doi.org/10.1016/S0024-3205(99)00441-5.
M.A. Barmade, P.R. Murumkar, M.K. Sharma and M.R. Yadav, Curr. Top. Med. Chem., 16, 2863 (2016); https://doi.org/10.2174/1568026616666160506145700.
W.M. El-Husseiny, M.A-A. El-Sayed, N.I. Abdel-Aziz, A.S. El-Azab, E.R. Ahmed and A.A.-M. Abdel-Aziz, J. Enzyme Inhib. Med. Chem., 33, 507 (2018); https://doi.org/10.1080/14756366.2018.1434519.
W.S. Hamama, M.E. Ibrahim, A.A. Gooda and H.H. Zoorob, J. Heterocycl. Chem., 55, 2623 (2018); https://doi.org/10.1002/jhet.3322.
H. Brahmbhatt, M. Molnar and V. Pavic, Karbala Int. J. Modern Sci., 4, 200 (2018); https://doi.org/10.1016/j.kijoms.2018.01.006.
J. Wang, H. Tang, B. Hou, P. Zhang, Q. Wang, B.-L. Zhang, Y.-W. Huang, Y. Wang, Z.-M. Xiang, C.-T. Zi, X.-J. Wang and J. Sheng, RSC Adv., 7, 54136 (2017); https://doi.org/10.1039/C7RA11496F.
A. Padmaja, T. Payani, G.D. Reddy and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009); https://doi.org/10.1016/j.ejmech.2009.06.024.
M. Prabhaharan, A.R. Prabakaran, S. Gunasekaran and S. Srinivasan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 123, 392 (2014); https://doi.org/10.1016/j.saa.2013.12.056.
J.B. Foresman and M. Frisch, Exploring Chemistry with Electronic Structure Methods, Gaussian Inc., Pittsburgh, edn 2 (1996).
W.S. Hamama, M.A. Gouda, M.H. Badr and H.H. Zoorob, Med. Chem. Res., 22, 3556 (2013); https://doi.org/10.1007/s00044-012-0336-z.