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Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

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Synthesis, Molecular Docking Studies, Antimicrobial, Anticancer and Antioxidant Activity of Some Novel Mannich Bases of Isatin Scaffold

https://doi.org/10.14233/ajchem.2022.23561
Kurni Lakshmi Deepthi
Department of Pharmacy, University College of Technology, Osmania University, Hyderabad-500010, India
N.J.P. Subhashini
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500010, India
T. Maneshwar
School of Pharmacy, Anurag University, Venkatapur, Ghatkesar, Hyderabad-500088, India

Corresponding Author(s) : Kurni Lakshmi Deepthi

deepthi.kurni@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

Abstract

A series of novel Mannich bases of isatin derivatives (VIIIa-VIIIt) was synthesized and evaluated as potential antimicrobial, antioxidant, anticancer activities and molecular docking studies. Structure of all the isatin derivatives was evaluated by IR, 1H NMR and mass spectral analysis. The antimicrobial activity results indicated that compounds VIIIb, VIIIi, VIIIm and VIIIo showed good activity in comparison to the activities of the standard molecules. Further, all isatin derivatives (VIIIa-VIIIt) have studied for their antioxidant activity by using ferric reducing antioxidant power assay (FRAP) method. Most of the synthesized compounds exhibited the significant antioxidant activities. The anticancer activity results suggested that the isatin derivatives VIIIm and VIIIg show the more activity against MCF-7 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of Mannich bases of isatin derivatives showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was inquisition.

Keywords

Iastin Iastin Benzaldehyde Benzaldehyde Ascorbic acid Ascorbic acid Antimicrobial Antioxidant activity Antimicrobial Antioxidant activity Anticancer activity Anticancer activity Molecular docking Molecular docking
Lakshmi Deepthi, K., Subhashini, N., & Maneshwar, T. (2022). Synthesis, Molecular Docking Studies, Antimicrobial, Anticancer and Antioxidant Activity of Some Novel Mannich Bases of Isatin Scaffold. Asian Journal of Chemistry, 34(5), 1097–1104. https://doi.org/10.14233/ajchem.2022.23561
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References
  1. Varun, Sonam and R. Kakkar, Med. Chem. Commun., 10, 351 (2019); https://doi.org/10.1039/c8md00585k
  2. G. Chen, Y. Wang, X. Hao, S. Mu and Q. Sun, Chem. Cent. J., 5, 37 (2011); https://doi.org/10.1186/1752-153X-5-37
  3. B.N. Shivabasappa and S.B. Jayaprakash, Int. J. Pharm. Pharm. Sci., 9, 128 (2017).
  4. V. Mehta, A. Sharma, P. Kailkhura and U. Malairaman, Asian J. Pharm. Clin. Res., 9, 44 (2016); https://doi.org/10.22159/ajpcr.2016.v9s3.14543
  5. G. Nagalakshmi, E-J. Chem., 5, 2 (2008); https://doi.org/10.1155/2008/921256
  6. R.E.F. de Paiva, E.G. Vieira, D.R. da Silva, C.A. Wegermann and A.M.C. Ferreira, Front. Mol. Biosci., 7, 627272 (2021); https://doi.org/10.3389/fmolb.2020.627272
  7. J. Jampilek, Molecules, 24, 3839 (2019); https://doi.org/10.3390/molecules24213839
  8. P.K. Sharma, S. Balwani, D. Mathur, S. Malhotra, B.K. Singh, A.K. Prasad, C. Len, E.V. Van der Eycken, B. Ghosh, N.G.J. Richards and V.S. Parmar, J. Enzyme Inhib. Med. Chem., 31, 1520 (2016); https://doi.org/10.3109/14756366.2016.1151015
  9. A. Gursoy and N. Karal, Eur. J. Med. Chem., 38, 633 (2003); https://doi.org/10.1016/S0223 5234(03)00085-0
  10. S.K. Sridhar and A. Ramesh, Biol. Pharm. Bull., 24, 1149 (2001); https://doi.org/10.1248/bpb.24.1149
  11. L. Endresen, Acta Pharm., 54, 49 (2009); https://doi.org/10.1111/j.1600-0773.1984.tb01894.x
  12. V. Glover, J.M. Halket, P.J. Watkins, A. Clow, B.L. Goodwin and M. Sandier, J. Neurochem., 51, 656 (1988); https://doi.org/10.1111/j.1471-4159.1988.tb01089.x
  13. H. Kumar, S.A. Javed, S.A. Khan and M. Amir, Eur. J. Med. Chem., 43, 2688 (2008); https://doi.org/10.1016/j.ejmech.2008.01.039
  14. M. Akhter, A. Husain, B. Azad and M. Ajmal, Eur. J. Med. Chem., 44, 2372 (2009); https://doi.org/10.1016/j.ejmech.2008.09.005
  15. G.A. Idrees, O.M. Aly, G. El-Din A.A. Abuo-Rahma and M.F. Radwan, Eur. J. Med. Chem., 44, 3973 (2009); https://doi.org/10.1016/j.ejmech.2009.04.026
  16. D.J. Bauer and P.W. Sadler, 1-Substituted Isatin-Thiosemicarbazones, their Preparation and Pharmaceutical Preparations containing them. Brit. Pat. 975357 (1964); Chem. Abstr., 62, 6462c (1965).
  17. D. Kumar, S. Sundaree, E.O. Johnson and K. Shah, Bioorg. Med. Chem. Lett., 19, 4492 (2009); https://doi.org/10.1016/j.bmcl.2009.03.172
  18. S. Muthusamy, S.A. Babu and M. Nethaji, Tetrahedron, 59, 8117 (2003); https://doi.org/10.1016/j.tet.2003.08.041
  19. M.M. Blanco, M.D. Maso, M.S. Shmidt and I.A. Perillo, Synthesis, 829 (2007); https://doi.org/10.1055/s-2007-965949
  20. R. Shakir, A. Ariffin and M. Abdulla, Molecules, 19, 3436 (2014); https://doi.org/10.3390/molecules19033436
  21. R.J. Ruch, S. Cheng and J.E. Klaunig, Carcinogenesis, 10, 1003 (1989); https://doi.org/10.1093/carcin/10.6.1003
  22. M.D. Shah, N.C. Desai, K.K. Awasthi and M.S. Saxena, Indian J. Chem., 40B, 201 (2001).
  23. K. Solankei and K. Kapadia, Orient. J. Chem., 17, 302 (2013).
  24. A. Venkanna, B. Siva, B. Poornima, P.R. Rao Vadaparthi, K.R. Prasad, K.A. Reddy, G.B.P. Reddy and K.S. Babu, Fitoterapia, 95, 102 (2014); https://doi.org/10.1016/j.fitote.2014.03.003
  25. Y. Kotaiah, N. Harikrishna, K. Nagaraju and C. Venkata Rao, Eur. J. Med. Chem., 58, 340 (2012); https://doi.org/10.1016/j.ejmech.2012.10.007
  26. L. Schrodinger, Schrodinger Software Suite, Schrödinger LLC: New York (2011).
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