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Vol. 34 No. 2 (2022): Vol 34 Issue 2

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Synthesis, Molecular Docking and DFT Studies of Biologically Active N-((3-(4-Nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)aniline Derivatives

https://doi.org/10.14233/ajchem.2022.23500
P.V SANDHYA
Department of Chemistry, Government R.W.P.C. Payyanur, Korom-670307, India
K.V. Satheesh Kumar
Department of Chemistry, Government College Kasaragod, Vidyanagar-671123, India
K.R. Haridas
Department of Chemistry, School of Chemical Sciences, Kannur University, Payyanur Campus, Edat-670327, India

Corresponding Author(s) : P.V SANDHYA

chemistryscs@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 2 (2022): Vol 34 Issue 2

Abstract

Some biologically active pyrazole clubbed imino molecules have been designed and synthesized from 1-phenyl-3-nitro phenyl-1H-pyrazol-4-carboxaldehyde and substituted aromatic amines via acid catalyzed condensation reaction. All the synthesized molecules were characterized by IR, 1H NMR, 13C NMR and mass spectral techniques. The in vitro antibactericidal property of the synthesized compounds was screened and compared with the results of theoretical molecular docking. Optimization of molecular geometry, DNA binding interaction and FMO analysis were also investigated by computational studies using Gaussian 16 package at B3LYP/6-31G(d,p) level. All the synthesized compounds exhibited moderate to good biological activities both experimentally and theoretically.

Keywords

Pyrazole derivatives Antibacterial activity Molecular docking DNA binding DFT studies
SANDHYA, P., Satheesh Kumar, K., & Haridas, K. (2022). Synthesis, Molecular Docking and DFT Studies of Biologically Active N-((3-(4-Nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)aniline Derivatives. Asian Journal of Chemistry, 34(2), 297–304. https://doi.org/10.14233/ajchem.2022.23500
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References
  1. M.D. Carrión, L.C. Lo’pez Cara, E.V. Camacho, M. Tapias, G. Escames, D. Acuña-Castroviejo, A. Espinosa, M.A. Gallo and A. Entrena, Eur. J. Med. Chem., 43, 2579 (2008); https://doi.org/10.1016/j.ejmech.2008.01.014
  2. N. Gökhan-Kelekçi, S. Koyunoglu, S. Yabanoglu, K. Yelekçi, Ö. Özgen, G. Uçar, K. Erol, E. Kendi and A. Yesilada, Bioorg. Med. Chem., 17, 675 (2009); https://doi.org/10.1016/j.bmc.2008.11.068
  3. J.V. Faria, P.F. Vegi, A.G.C. Miguita, M.S. dos Santos, N. Boechat and A.M.R. Bernardino, Bioorg. Med. Chem., 25, 5891 (2017); https://doi.org/10.1016/j.bmc.2017.09.035
  4. M. Abid, A.R. Bhat, F. Athar and A. Azam, Eur. J. Med. Chem., 44, 417 (2009); https://doi.org/10.1016/j.ejmech.2007.10.032
  5. A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 881 (2008); https://doi.org/10.1016/j.bmc.2007.10.015
  6. S.R. Shih, T.Y. Chu, G.R. Reddy, S.-N. Tseng, H.-L. Chen, W.-F. Tang, M. Wu, J.-Y. Yeh, Y.-S. Chao, J.T.A. Hsu, H.-P. Hsieh and J.-T. Horng, J. Biomed. Sci., 17, 13 (2010); https://doi.org/10.1186/1423-0127-17-13
  7. H. Naito, S. Ohsuki, M. Sugimori, R. Atsumi, M. Minami, Y. Nakamura, M. Ishii, K. Hirotani, E. Kumazawa and A. Ejima, Chem. Pharm. Bull. (Tokyo), 50, 453 (2002); https://doi.org/10.1248/cpb.50.453
  8. M. Abdel-Aziz, G.A. Abuo-Rahma and A.A. Hassan, Eur. J. Med. Chem., 44, 3480 (2009); https://doi.org/10.1016/j.ejmech.2009.01.032
  9. A.M. Farag, A.S. Mayhoub, S.E. Barakat and A.H. Bayomi, Bioorg. Med. Chem., 16, 4569 (2008); https://doi.org/10.1016/j.bmc.2008.02.043
  10. K. Karrouchi, S. Radi, Y. Ramli, J. Taoufik, Y.N. Mabkhot, F.A. AlAizari and M. Ansar, Molecules, 23, 134 (2018); https://doi.org/10.3390/molecules23010134
  11. E.G. Chalina and L. Chakarova, Eur. J. Med. Chem., 33, 975 (1998); https://doi.org/10.1016/S0223-5234(99)80022-1
  12. V. Michon, C.H. du Penhoat, F. Tombret, J.M. Gillardin, F. Lepage and L. Berthon, Eur. J. Med. Chem., 30, 147 (1995); https://doi.org/10.1016/0223-5234(96)88220-1
  13. R.V. Ragavan, V. Vijayakumar and N.S. Kumari, Eur. J. Med. Chem., 45, 1173 (2010); https://doi.org/10.1016/j.ejmech.2009.12.042
  14. M.J. Alam, O. Alam, P. Alam and M.J. Naim, Int. J. Pharm. Sci. Res., 6, 1433 (2015).
  15. H.A. Saad, N.A. Osman and A.H. Moustafa, Molecules, 16, 10187 (2011); https://doi.org/10.3390/molecules161210187
  16. A. Balbi, M. Anzaldi, M. Mazzei, M. Miele, M. Bertolotto, L. Ottonello and F. Dallegri, Bioorg. Med. Chem., 14, 5152 (2006); https://doi.org/10.1016/j.bmc.2006.04.007
  17. G.M. Hill, D.M. Moriarity and W.N. Setzer, Sci. Pharm., 79, 729 (2011); https://doi.org/10.3797/scipharm.1107-19
  18. N.C. Desai, A. Dodiya and N. Shihory, J. Saudi Chem. Soc., 17, 259 (2013); https://doi.org/10.1016/j.jscs.2011.04.001
  19. A.S. Khalil and J.J. Collins, Nat. Rev. Genet., 11, 367 (2010); https://doi.org/10.1038/nrg2775
  20. C. Zhang, S. Chang, X. Tian and Y. Tian, Asian J. Chem., 26, 264 (2014); https://doi.org/10.14233/ajchem.2014.15883
  21. I. Çetin, P.E. Elma, M. Topçul and N. Karali, Istanbul J. Pharm., 48, 63 (2018); https://doi.org/10.26650/IstanbulJPharm.2018.414805
  22. A. Pai, D.V. Kumar and B.S. Jayashree, Asian J. Pharm. Sci., 11, 187 (2016); https://doi.org/10.1016/j.ajps.2015.11.044
  23. D. Ravi, S. Sarkar, S. Purvey, F. Passero, A. Beheshti, Y. Chen, M. Mokhtar, K. David, T. Konry and A.M. Evens, Leukemia, 34, 1291 (2020); https://doi.org/10.1038/s41375-019-0663-x
  24. M.M. de Oliveira Cabral, P.M. Mendonça, C.M.S. Gomes, J.M. Barbosa-Filho, C.S. Dias, M.J. Soares and M.M. de Carvalho Queiroz, J. Med. Entomol., 44, 249 (2007); https://doi.org/10.1093/jmedent/44.2.249
  25. G. Kapoor, S. Saigal and A. Elongavan, J. Anaesthesiol. Clin. Pharmacol., 33, 300 (2017); https://doi.org/10.4103/joacp.JOACP_349_15
  26. Q. Cui, W. S. Shin, Y. Luo, J. Tian, H. Cui and D. Yin, Curr. Med. Chem., 20, 1286 (2013); https://doi.org/10.2174/0929867311320100006
  27. R. Rohs, I. Bloch, H. Sklenar and Z. Shakked, Nucleic Acids Res., 33, 7048 (2005); https://doi.org/10.1093/nar/gki1008
  28. M. Baginski, F. Fogolari and J.M. Briggs, J. Mol. Biol., 274, 253 (1997); https://doi.org/10.1006/jmbi.1997.1399
  29. E.M. Proudfoot, J.P. Mackay and P. Karuso, Biochemistry, 40, 4867 (2001); https://doi.org/10.1021/bi001655f
  30. R. Corradini, S. Sforza, T. Tedeschi and R. Marchelli, Chirality, 19, 269 (2007); https://doi.org/10.1002/chir.20372
  31. J. Lakshmipraba, S. Arunachalam, R.V. Solomon and P. Venuvanalingam, J. Coord. Chem., 68, 1374 (2015); https://doi.org/10.1080/00958972.2015.1014349
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