Issue

Vol. 33 No. 10 (2021): Vol 33 Issue 10, 2021

Copyright (c) 2021 AJC

Creative Commons License

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

Synthesis, Biological Evaluation and Docking Studies of 1,2,4,5-Tetrasubstituted Imidazoles as Antibacterial Agents: Use of Niobia Supported Heteropoly Tungstate as an Efficient Reusable Catalyst

https://doi.org/10.14233/ajchem.2021.23181
Aravind Kurnool
Department of Chemistry, Central Main Research Lab, Osmania University, Hyderabad-500007, India
Karunasree Merugu
Department of Chemistry, GITAM University, Bengaluru Campus, Bengaluru-560034, India
Pachipulusu Shravya
Department of Chemistry, GITAM University, Bengaluru Campus, Bengaluru-560034, India
P. Malleswarareddy
Department of Chemistry, S.K. University, Anantapuramu-515003, India

Corresponding Author(s) : Karunasree Merugu

kmerugu@gitam.edu

Asian Journal of Chemistry, Vol. 33 No. 10 (2021): Vol 33 Issue 10, 2021

Abstract

The synthesis of novel 1,2,4,5-tetrasubstituted imidazoles was carried out in a single molecular motif using niobia supported heteropoly tungstate as a mild and efficient reusable catalyst. The condensation of 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehyde, aromatic amine, benzil, ammonium acetate and heteropoly tungstate supported on niobia was achieved under both conventional and non-conventional conditions. The employed protocol provides significant advantages, as it exhibits a remarkable catalytic activity on recovery, excellent yields and excellent reaction efficacy within short reaction times between 1-2 h (conventional) and 1-3 min (microwave radiation). All the obtained compounds were characterized by means of spectral data and elemental analysis. They were also screened for their antibacterial activity. To predict the binding mode of compounds with glutamine-fructose-6-phosphate transaminase (GlcN6P synthase), docking studies were performed.

Keywords

Tungstophosphoric acid Microwave irradiation Antibacterial agents 1,2,4,5-Tetrasubstituted imidazoles
Kurnool, A., Merugu, K., Shravya, P., & Malleswarareddy, P. (2021). Synthesis, Biological Evaluation and Docking Studies of 1,2,4,5-Tetrasubstituted Imidazoles as Antibacterial Agents: Use of Niobia Supported Heteropoly Tungstate as an Efficient Reusable Catalyst. Asian Journal of Chemistry, 33(10), 2423–2429. https://doi.org/10.14233/ajchem.2021.23181
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. D.A. Shabalin and J.E. Camp, Org. Biomol. Chem., 18, 3950 (2020); https://doi.org/10.1039/D0OB00350F
  2. L. Zhang, X.-M. Peng, G.L.V. Damu, R.-X. Geng and C.-H. Zhou, Med. Res. Rev., 34, 340 (2014); https://doi.org/10.1002/med.21290
  3. G.K. Wagner, D. Kotschenreuther, W. Zimmermann and S.A. Laufer, J. Org. Chem., 68, 4527 (2003); https://doi.org/10.1021/jo026619w
  4. L. Ruilope, B. Jager and B. Prichard, Blood Press., 10, 223 (2001); https://doi.org/10.1080/08037050152669747
  5. S.L. Abrahams, R.J. Hazen, A.G. Batson and A.P. Phillips, J. Pharmacol. Exp. Ther., 249, 359 (1989).
  6. S. Dini, G.F. Caselli, C. Basilico, A. Lavezzo and R. Giani, Agents Actions, 30, 174 (1990); https://doi.org/10.1007/BF01969030
  7. U. Ucucu, N.G. Karaburun and I. Isikdag, Il Farmaco, 56, 285 (2001); https://doi.org/10.1016/S0014-827X(01)01076-X
  8. G. Ronsisvalle, M.S. Pappalardo, F. Vittorio, L. Pasquinucci, E. Bousquet, S. Oliveri and E. Cammarata, Il Farmaco, 44, 383 (1989).
  9. A.M. Vijesh, A.M. Isloor, S. Telkar, T. Arulmoli and H.-K. Fun, Arab. J. Chem., Arab. J. Chem., 6, 197 (2013); https://doi.org/10.1016/j.arabjc.2011.10.007
  10. B. Naziyanaz, Arab. J. Chem., 9(suppl. 1), S100 (2016); https://doi.org/10.1016/j.arabjc.2011.02.013
  11. C.F. Claiborne, N.J. Liverton and K.T. Nguyen, Tetrahedron Lett., 39, 8939 (1998); https://doi.org/10.1016/S0040-4039(98)02058-9
  12. C. Zhang, S. Sarshar, E.J. Moran, S. Krane, J.C. Rodarte, K.D. Benbatoul, R. Dixon and A.M.M. Mjalli, Bioorg. Med. Chem., 10, 2603 (2000); https://doi.org/10.1016/S0960-894X(00)00521-7
  13. S. Balalaie and A. Arabanian, Green Chem., 2, 274 (2000); https://doi.org/10.1039/b006201o
  14. Q.-X. Guo, Y. Xu, Y.-Z. Liu, L. Rui and L. Liu, Heterocycles, 63, 87 (2004); https://doi.org/10.3987/COM-03-9896
  15. A.R. Karimi, Z. Alimohammadi, J. Azizian, A.A. Mohammadi and M.R. Mohammadizadeh, Catal. Commun., 7, 728 (2006); https://doi.org/10.1016/j.catcom.2006.04.004
  16. M.M. Heravi, F. Derikvand and F.F. Bamoharram, J. Mol. Catal. Chem., 263, 112 (2007); https://doi.org/10.1016/j.molcata.2006.08.048
  17. E. Gelens, F.J.J.D. Kanter, R.F. Schmitz, L.A.J.M. Sliedregt, B.J.V. Steen, C.G. Kruse, R. Leurs, M.B. Groen and R.V.A. Orru, Mol. Divers., 10, 17 (2006); https://doi.org/10.1007/s11030-006-8695-3
  18. D.R.J. Acke, R.V.A. Orru and C.V. Stevens, QSAR Comb. Sci., 25, 474 (2006); https://doi.org/10.1002/qsar.200540194
  19. M. Kidwai, S. Saxena, Ruby and S. Rastogi, Bull. Korean Chem. Soc., 26, 2051 (2005); https://doi.org/10.5012/bkcs.2005.26.12.2051
  20. M. Kidwai and P. Mothsra, Tetrahedron Lett., 47, 5029 (2006); https://doi.org/10.1016/j.tetlet.2006.05.097
  21. A.Y.U. Usyatinsky and Y.L. Khmelnitsky, Tetrahedron Lett., 41, 5031 (2000); https://doi.org/10.1016/S0040-4039(00)00771-1
  22. L. Nagarapu, S. Apuri and S. Kantevari, J. Mol. Catal. Chem., 266, 104 (2007); https://doi.org/10.1016/j.molcata.2006.10.056
  23. L. Nagarapu, S. Kantevari, V.C. Mahankhali and S. Apuri, Catal. Commun., 8, 1173 (2007); https://doi.org/10.1016/j.catcom.2006.11.003
  24. L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri and N. Vijaya Kumari, J. Mol. Catal. Chem., 264, 22 (2007); https://doi.org/10.1016/j.molcata.2006.09.001
  25. The United States Pharmacopoeia, Biological Tests and Assay, Rockwille: MD, USA, Ed. 25 (2001).
  26. Maestro, version 9.2; Schrodinger, LLC: New York, NY (2012).
  27. S. Mouilleron, M.A. Badet-Denisot and B. Golinelli-Pimpaneau, J. Mol. Biol., 377, 1174 (2008); https://doi.org/10.1016/j.jmb.2008.01.077
  28. Glide, version 5.7; Schrodinger, LLC: New York, NY (2012)
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0