Issue

Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Copyright (c) 2024 Shipra Gautam, Poonam Rawat, Prakash, Anant Ram, Amul Darwari, Sharda Pandey, Anupama Pandey, RamNiwas Singh

Creative Commons License

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

Ecofriendly Synthesis, Spectroscopic Analysis and in silico Study of Coumarin Hydrazide-Hydrazone Derivative Targeted against HIV and SARS-CoV-2

https://doi.org/10.14233/ajchem.2024.32117
Shipra Gautam
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0009-0003-3120-7303
Poonam Rawat
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0000-0003-0365-7633
Prakash
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0000-0002-3533-9624
Anant Ram
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0009-0002-4481-6362
Amul Darwari
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0009-0000-2785-0089
Sharda Pandey
Department of Physics, University of Lucknow, Lucknow-226007, India
https://orcid.org/0000-0001-9950-1195
Anupama Pandey
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0009-0009-5931-1739
R.N. Singh
Department of Chemistry, University of Lucknow, Lucknow-226007, India
https://orcid.org/0000-0003-3459-2254

Corresponding Author(s) : R.N. Singh

rnsvk.chemistry@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 9 (2024): Vol 36 Issue 9, 2024

Abstract

Coumarin based hydrazide-hydrazone (CHH) derivative was synthesized and evaluated for in silico antiviral activity against SARS-CoV-2 and anti-HIV activity. The experimental techniques (FT-IR, 1H NMR, 13C NMR and UV-vis) and computational calculations (B3LYP functional and 6-31G(d,p)/6-311G(d,p) level of theory) were used for the detailed analysis of the synthesized compound. By following the mechanosynthesis methodology, the excellent yield and reduction in reaction time were observed in the grinding method when compared to conventional method. The rotational barrier between conformer I and II of CHH was found to be 5.102 Kcal/mol in the gas phase. The FT-IR spectrum was carried out to support the hydrogen bonding pattern proposed by reported crystalline structure. The electronic descriptors studies indicate CHH used as useful synthon for new heterocyclic compounds. The first static hyperpolarizability (β0) of the CHH was calculated as 17.47 and 25.93 10–30 esu at B3LYP/6-31G (d,p) and B3LYP/6-311G(d,p) basis set indicates CHH may be used as non-linear optical material. The ADMET, isoelectronic molecular electrostatic potential surfaces (MEPS), NBO and QTAIM studies were also performed. According to molecular docking, the synthesized CHH compound showed strong antiviral efficacy against SARS COV-2 major protein (Mpro) with PDB code 6lu7 and anti-HIV antibody DH501, an unmutated common ancestor with PDB ID 6p3b.

Keywords

Coumarin Hydrazide-hydrazone Mechanosynthesis Antiviral activity ADMET QTAIM
Gautam, S., Rawat, P., Prakash, Ram, A., Darwari, A., Pandey, S., … Singh, R. (2024). Ecofriendly Synthesis, Spectroscopic Analysis and in silico Study of Coumarin Hydrazide-Hydrazone Derivative Targeted against HIV and SARS-CoV-2. Asian Journal of Chemistry, 36(9), 2097–2114. https://doi.org/10.14233/ajchem.2024.32117
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. D.J. Newman and G.M. Cragg, J. Nat. Prod., 83, 770 (2020); https://doi.org/10.1021/acs.jnatprod.9b01285
  2. Q.C. Ren, C. Gao, Z. Xu, L.S. Feng, M.L. Liu, X. Wu and F. Zhao, Curr. Top. Med. Chem., 18, 101 (2018); https://doi.org/10.2174/1568026618666180221114515
  3. T. Abe, Y. Marutani and I. Shoji, Microbiol. Immunol., 63, 51 (2019); https://doi.org/10.1111/1348-0421.12669
  4. Y. Hu, W. Chen, Y. Shen, B. Zhu and G.X. Wang, Bioorg. Med. Chem. Lett., 29, 1749 (2019); https://doi.org/10.1016/j.bmcl.2019.05.019
  5. T.M. Khomenko, V.V. Zarubaev, I.R. Orshanskaya, R.A. Kadyrova, V.A. Sannikova, D.V. Korchagina, K.P. Volcho and N.F. Salakhutdinov, Bioorg. Med. Chem. Lett., 27, 2920 (2017); https://doi.org/10.1016/j.bmcl.2017.04.091
  6. L. De Luca, F.E. Agharbaoui, R. Gitto, M.R. Buemi, F. Christ, Z. Debyser and S. Ferro, Mol. Inform., 35, 460 (2016); https://doi.org/10.1002/minf.201501034
  7. T.O. Olomola, R. Klein, N. Mautsa, Y. Sayed and P.T. Kaye, Bioorg. Med. Chem., 21, 1964 (2013); https://doi.org/10.1016/j.bmc.2013.01.025
  8. P. Zhou, Y. Takaishi, H. Duan, B. Chen, G. Honda, M. Itoh, Y. Takeda, O.K. Kodzhimatov and K.H. Lee, Phytochemistry, 51, 781 (2000); https://doi.org/10.1016/S0031-9422(99)00554-3
  9. C.I. Paules, H.D. Marston and A.S. Fauci, JAMA, 323, 707 (2020); https://doi.org/10.1001/jama.2020.0757
  10. S. Mishra, A. Pandey and S. Manvati, Heliyon, 6, e03217 (2020); https://doi.org/10.1016/j.heliyon.2020.e03217
  11. M.Z. Hassan, H. Osman, M.A. Ali and M.J. Ahsan, Eur. J. Med. Chem., 123, 236 (2016); https://doi.org/10.1016/j.ejmech.2016.07.056
  12. K.N. Venugopala, V. Rashmi and B. Odhav, BioMed Res. Int., 2013, 963248 (2013); https://doi.org/10.1155/2013/963248
  13. Y. Shikishima, Y. Takaishi, G. Honda, Y. Takeda, O.K. Kodzhimatov, M. Ito, O. Ashurmetov and K.H. Lee, Chem. Pharm. Bull., 49, 877 (2001); https://doi.org/10.1248/cpb.49.877
  14. N. Márquez, R. Sancho, L.M. Bedoya, J. Alcamí, J.L. López-Pérez, A. San Feliciano, B.L. Fiebich and E. Muñoz, Antivir. Res., 66, 137 (2005); doi.org/10.1016/j.antiviral. 2005. 02.006
  15. N.F. Holguín, J. Frau and D.G. Mitnik, Front Chem., (2021); https://doi.org/10.3389/fchem.2021.708364
  16. S. Yadav, S. Singh and C. Gupta, Curr. Res. Green Sust. Chem., 5, 100260 (2022); https://doi.org/10.1016/j.crgsc.2022.100260
  17. M. Molnar, M. Lonèariæ and M. Kovaè, Curr. Org. Chem., 24, 4 (2020); https://doi.org/10.2174/1385272824666200120144305
  18. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A.V. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M.J. Bearpark, J.J. Heyd, E.N. Brothers, K.N. Kudin, V.N. Staroverov, T.A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.P. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman and D.J. Fox, Gaussian, Inc. Wallingford CT (2010).
  19. A.D. Becke, J. Chem. Phys., 98, 5648 (1993); https://doi.org/10.1063/1.464913
  20. C.T. Lee, W.T. Yang and R.G.B. Parr, Phys. Rev. B Condens. Matter, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785
  21. G.A. Petersson and M.A. Al-laham, J. Chem. Phys., 94, 6081 (1991); https://doi.org/10.1063/1.460447
  22. G.A. Petersson, A. Bennett, T.G. Tensfeldt, M.A. AlLaham, W.A. Shirley and J. Mantzaris, J. Chem. Phys., 89, 2193 (1988); https://doi.org/10.1063/1.455064
  23. K.C. Mariamma, H.T. Varghese, C.Y. Panicker, K. John, J. Vinsova and C. Van Alsenoy, Spectrochim. Acta A Mol. Biomol. Spectrosc., 112, 161 (2013); https://doi.org/10.1016/j.saa.2013.04.052
  24. K.N. Chethan Prathap and N.K. Lokanath, J. Mol. Struct., 1158, 26 (2018); https://doi.org/10.1016/j.molstruc.2018.01.007
  25. A.P. Scott and L. Radom, J. Phys. Chem., 100, 16502 (1996); https://doi.org/10.1021/jp960976r
  26. NIST Computational Chemistry Comparison and Benchmark Database NIST Standard Reference Database Number 101, Russell D. Johnson III (2022); https://doi.org/10.18434/T47C7Z
  27. R. Alphonse, A. Varghese, L. George and A. Nizam, J. Mol. Liq., 215, 387 (2016); https://doi.org/10.1016/j.molliq.2015.12.050
  28. R.G. Pearson, Chemical Hardness: Applications from Molecules to Solids Wiley- VCH, Weinheim, Germany (1997).
  29. R.E. Aderne, B.G.A.L. Borges, H.C. Ávila, F. von Kieseritzky, J. Hellberg, M. Koehler, M. Cremona, L.S. Roman, C.M. Araujo, M.L.M. Rocco and C.F.N. Marchiori, Mater. Adv., 3, 1791 (2022); https://doi.org/10.1039/D1MA00652E
  30. M. Snehalatha, C. Ravikumar, I. Hubert Joe, N. Sekar and V.S. Jayakumar, Spectrochim. Acta A Mol. Biomol. Spectrosc., 72, 654 (2009); https://doi.org/10.1016/j.saa.2008.11.017
  31. D.W. Schwenke and D.G. Truhlar, J. Chem. Phys., 82, 2418 (1985); https://doi.org/10.1063/1.448335
  32. M. Gutowski, J.G.C.M. Van Duijneveldt-Van de Rijdt, J.H. Van Lenthe and F.B. Van Duijneveldt, J. Chem. Phys., 98, 4728 (1993); https://doi.org/10.1063/1.465106
  33. F. Weinhold, C.R. Landis and E.D. Glendening, Int. Rev. Phys. Chem., 35, 399 (2016); https://doi.org/10.1080/0144235X.2016.1192262
  34. D.A. Kleinman, Phys. Rev., 126, 1977 (1962); https://doi.org/10.1103/PhysRev.126.1977
  35. H. Alyar, Z. Kantarci, M. Bahat and E. Kasap, J. Mol. Struct., 834-836, 516 (2007); https://doi.org/10.1016/j.molstruc.2006.11.066
  36. J.L. Oudar and D.S. Chemla, J. Chem. Phys., 66, 2664 (1977); https://doi.org/10.1063/1.434213
  37. N. Sukumar, A Matter of Density: Exploring the Electron Density Concept in the Chemical, Biological, and Materials Sciences, Wiley-Blackwell (2012).
  38. P. Rawat and R.N. Singh, Spectrochim. Acta A Mol. Biomol. Spectrosc., 140, 344 (2015); https://doi.org/10.1016/j.saa.2014.12.080
  39. R.G. Parr, L. Szentpály and S. Liu, J. Am. Chem. Soc., 121, 1922 (1999); https://doi.org/10.1021/ja983494x
  40. R.G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York (1989).
  41. A. Daina, O. Michielin and V. Zoete, Sci. Rep., 7, 42717 (2017); https://doi.org/10.1038/srep42717
  42. M. Alsawalha, S.R. Bolla, N. Kandakatla, V. Srinivasadesikan, V.P. Veeraraghavan and K.M. Surapaneni, Bioinform., 15, 380 (2019); https://doi.org/10.6026/97320630015380
  43. R. Yuan, S. Madani, X.X. Wei, K. Reynolds and S.M. Huang, Drug Metab. Dispos., 30, 1311 (2002); https://doi.org/10.1124/dmd.30.12.1311
  44. J.E. McGraw, A Handbook of Pharmacogenomics and Stratified Medicine, Elsevier Publication (2014).
  45. F. Cheng, W. Li, Y. Zhou, J. Shen, Z. Wu, G. Liu, P.W. Lee and Y.T. Admet, J. Chem. Inf. Mod., 52, 3099 (2012); https://doi.org/10.1021/ci300367a
  46. M.M. Julie, T. Prabhu, E. Elamuruguporchelvi, F.B. Asif, S. Muthu and A. Irfan, J. Mol. Liq., 336, 116335 (2021); https://doi.org/10.1016/j.molliq.2021.116335
  47. L. Schrödinger and W. DeLano, PyMOL. 2020; http://www.pymol.org/pymol
  48. https://www.ebi.ac.uk/thornton-srv/databases/pdbsum/
  49. A.T. Dubis, S.J. Grabowski, D.B. Romanowska, T. Misiaszek and J. Leszczynski, J. Phys. Chem. A, 106, 10613 (2002); https://doi.org/10.1021/jp0211786
Read More
Author biographies is not available.
Statistic
Read Counter : 0 Download : 0