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Vol. 32 No. 3 (2020): Vol 32 Issue 3

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Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity

https://doi.org/10.14233/ajchem.2020.22390
D. Sam Daniel Prabu
Department of Chemistry, Presidency College, Chennai-600005, India
Sivalingam Lakshmanan
Department of Chemistry, BIHER, Bharath University, Chennai-600073, India
K. Thirumurugan
Department of Chemistry, Presidency College, Chennai-600005, India
N. Ramalakshmi
Department of Chemistry, Presidency College, Chennai-600005, India
S. Arul Antony
Department of Chemistry, Presidency College, Chennai-600005, India

Corresponding Author(s) : N. Ramalakshmi

rrama_subhar@yahoo.co.in

Asian Journal of Chemistry, Vol. 32 No. 3 (2020): Vol 32 Issue 3

Abstract

A series of febuxostat based new chemical entities was synthesized using microwave method and characterized by NMR, mass and FT-IR spectral studies. Molecular docking of febuxostat amide nucleus substitution compounds 8c (-7.91 kcal/mol), 8g (-7.94 kcal/mol) exhibiting high binding energy against ALK receptors. Theoretical investigation of MEPs, HOMO, LUMO and energy gap of HOMO-LUMO were calculated by B3LYP/6-31G method. Among the tested compounds, methoxy substituted compound 8g showed highest antibacterial activity against S. aereus and B. subtilis.

Keywords

Microwave method Febuxostat amides Antibacterial activity DFT study
Daniel Prabu, D. S., Lakshmanan, S., Thirumurugan, K., Ramalakshmi, N., & Antony, S. A. (2020). Synthesis, Molecular Docking, DFT Study of Novel N-Benzyl-2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxamide Derivatives and their Antibacterial Activity. Asian Journal of Chemistry, 32(3), 619–626. https://doi.org/10.14233/ajchem.2020.22390
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References
  1. S. Singh, P. Parashar, J. Kanoujia, I. Singh, S. Saha and S.A. Saraf, J. Drug Delivery Sci. Tech., 39, 348 (2017); https://doi.org/10.1016/j.jddst.2017.04.020
  2. K. Okamoto, B. Egers, T. Nishino and E. Pai, J. Biol. Chem., 278, 1848 (2003); https://doi.org/10.1074/jbc.M208307200
  3. Y. Osada, M. Tsuchimoto, H. Fukushima, K. Takahashi, S. Kondo, M. Hasegawa and K. Komoriya, Eur. J. Pharmacol., 241, 183 (1993); https://doi.org/10.1016/0014-2999(93)90201-R
  4. T. Hosoya, Y. Ogawa, H. Hashimoto, T. Ohashi and R. Sakamoto, J. Clin. Pharm. Ther., 41, 290 (2016); https://doi.org/10.1111/jcpt.12391
  5. K. Komoriya, Y. Osada, M. Hasegawa, H. Horiuchi, S. Kondo, R.C. Couch and T.B. Griffin, Eur. J. Pharmacol., 250, 455 (1993); https://doi.org/10.1016/0014-2999(93)90033-E
  6. S. Mitsuboshi, H. Yamada, K. Nagai and H. Okajima, Biol. Pharm. Bull., 40, 1463 (2017); https://doi.org/10.1248/bpb.b17-00284
  7. H.J. Tang, L. Yang, W. Li and J.H. Li, Chen, RSC Adv., 6, 113527 (2016); https://doi.org/10.1039/C6RA24396G
  8. P. Pacher, A. Nivorozhkin and C. Szabo, Pharmacol. Rev., 58, 87 (2006); https://doi.org/10.1124/pr.58.1.6.
  9. J.R. Li., D.D. Li, R.R. Wang, J. Sun, J.J. Dong, Q. R. Du, F. Fang, W.M. Zhang and H. L. Zhu, Eur. J. Med. Chem., 75, 438 (2014); https://doi.org/10.1016/j.ejmech.2013.11.020
  10. K.H. Patel and A.G. Mehta, Eur. J. Chem., 3, 885 (2006).
  11. A. Ayati, S. Emami, A. Asadipour, A. Shafiee and A. Foroumadi, Eur. J. Med. Chem., 97, 699 (2015); https://doi.org/10.1016/j.ejmech.2015.04.015
  12. T. Srivastava, A. Gaikwad, W. Haq, S. Sinha and B.S. Katti, Arkivoc, 120 (2005); https://doi.org/10.3998/ark.5550190.0006.209
  13. H.A. Taha and M.I. Soliman, Int. J. Agric. Biol., 1, 87 (2007).
  14. I. Vazzan, E. Terranov, F. Mattioli and F. Sparatore, Arkivoc, 364 (2004); https://doi.org/10.3998/ark.5550190.0005.531
  15. W.C. Patt, H.W. Hamilton, M.D. Taylor, M.J. Ryan, D.G. Taylor, C.J. Connolly, A.M. Doherty, S.R. Klutchko, I. Sircar, B.A. Steinbaugh, B.L. Batley, C.A. Painchaud, S.T. Rapundalo, B.M. Michniewicz and S.C.J. Olson, J. Med. Chem., 35, 2562 (1992); https://doi.org/10.1021/jm00092a006.
  16. F.W. Bell, A.S. Cantrell, M. Hogberg, S.R. Jaskunas, N.G. Johansson, C.L. Jordan, M.D. Kinnick, P. Lind, J.M. Morin, R. Noreen, B. Oberg, J.A. Palkowitz, C.A. Parrish, P. Pranc, C. Sahlberg, R.J. Ternansky, R.T. Vasileff, L. Vrang, S.J. West, H. Zhang and X.X. Zhou, J. Med. Chem., 38, 4929 (1995); https://doi.org/10.1021/jm00025a010
  17. N. Ergenc, G. Capan, N.S. Gunay, S. Ozkirimli, M. Gungor, S. Ozbey and E. Kendi, Arch. Pharm. Pharm. Med. Chem., 332, 343 (1999); https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AIDARDP343>3.3.CO;2-S.
  18. S. Fletcher, E.P. Keaney, C.G. Cummings, M.A. Blaskovich, M.A. Hast, M.P. Glenn, S.Y. Chang, C.J. Bucher, R.J. Floyd, W.P. Katt, M.H. Gelb, W.C. Van Voorhis, L.S. Beese, S.M. Sebti and A.D. Hamilton, J. Med. Chem., 53, 6867 (2010); https://doi.org/10.1021/jm1001748
  19. Y.S. Yang, F. Zhang, C. Gao, Y.B. Zhang, X.L. Wang, J.F. Tang, J. Sun, H.B. Gong and H.L. Zhu, Bioorg. Med. Chem. Lett., 22, 4619 (2012); https://doi.org/10.1016/j.bmcl.2012.05.091
  20. P.C. Lv, K.R. Wang, Y. Yang, W.J. Mao, J. Chen and J. Xiong, Bioorg. Med. Chem. Lett., 19, 6750 (2009); https://doi.org/10.1016/j.bmcl.2009.09.111
  21. E.L. Kwak, Y.J. Bang and D.R. Camidge, A.T. Shaw, B. Solomon, R.G. Maki, S.-H.I. Ou, B.J. Dezube, P.A. Jänne, D.B. Costa, M. VarellaGarcia, W.-H. Kim, T.J. Lynch, P. Fidias, H. Stubbs, J.A. Engelman, L.V. Sequist, M.P.H. WeiWei Tan, L. Gandhi, M. Mino-Kenudson, G.C. Wei, S.M. Shreeve, M.J. Ratain, J. Settleman, J.G. Christensen, D.A. Haber, K. Wilner, R. Salgia, G.I. Shapiro, J.W. Clark and A.J. Iafrate, N. Engl. J. Med., 363, 1693 (2010); https://doi.org/10.1056/NEJMoa1006448
  22. C.G. Passerini, C. Messa and E.M. Pogliani, N. Engl. J. Med., 364, 775 (2011); https://doi.org/10.1056/NEJMc1013224
  23. T.R. Webb, J. Slavish, R.E. George, A.T. Look, L. Xue, Q. Jiang, X. Cui, W.B. Rentrop and S.W. Morris, Expert Rev. Anticancer Ther., 9, 331 (2009); https://doi.org/10.1586/14737140.9.3.331
  24. M. Soda, Y.L. Choi, M. Enomoto, S. Takada, Y. Yamashita, S. Ishikawa, S. Fujiwara, H. Watanabe, K. Kurashina, H. Hatanaka, M. Bando, S. Ohno, Y. Ishikawa, H. Aburatani, T. Niki, Y. Sohara, Y. Sugiyama and H. Mano, Nature, 448, 561 (2007); https://doi.org/10.1038/nature05945
  25. K. Rikova, A. Guo, Q. Zeng, A. Possemato, J. Yu, H. Haack, J. Nardone, K. Lee, C. Reeves, Y. Li, Y. Hu, Z. Tan, M. Stokes, L. Sullivan, J. Mitchell, R. Wetzel, J. MacNeill, J.M. Ren, J. Yuan, C.E. Bakalarski, J. Villen, J.M. Kornhauser, B. Smith, D. Li, X. Zhou, S.P. Gygi, T.-L. Gu, R.D. Polakiewicz, J. Rush and M.J. Comb, Cell, 131, 1190 (2007); https://doi.org/10.1016/j.cell.2007.11.025
  26. D.R. Camidge and R.C. Doebele, Nat. Rev. Clin. Oncol., 9, 268 (2012); https://doi.org/10.1038/nrclinonc.2012.43
  27. F.H. Blackhall, S. Peters, L. Bubendorf, U. Dafni, K.M. Kerr, H. Hager, A. Soltermann, K.J. O'Byrne, C. Dooms, A. Sejda, J. Hernández-Losa, A. Marchetti, S. Savic, Q. Tan, E. Thunnissen, E.-J.M. Speel, R. Cheney, D. Nonaka, J. de Jong, M. Martorell, I. Letovanec, R. Rosell and R.A. Stahel, Ann. Oncol., 23, 73 (2012); https://doi.org/10.1200/JCO.2013.54.5921
  28. F. Bray, S.J. Ren, E. Masuyer and J. Ferlay, Int. J. Canc., 132, 1133 (2013); https://doi.org/10.1002/ijc.27711
  29. R.L. Siegel, K.D. Miller and A. Jemal, Cancer J. Clin., 66, 7 (2016); https://doi.org/10.3322/caac.21332
  30. W.C. Wang, H.Y. Shiao, C.C. Lee, S.K. Fung and H.P. Hsieh, Med. Chem. Commun., 5, 1266 (2014); https://doi.org/10.1039/C4MD00048J
  31. S.-H.I. Ou, E.L. Kwak, C. Siwak-Tapp, J. Dy, K. Bergethon, J.W. Clark, D.R. Camidge, B.J. Solomon, R.G. Maki, Y.-J. Bang, D.-W. Kim, J. Christensen, W. Tan, K.D. Wilner, R. Salgia and A.J. Iafrate, J. Thorac. Oncol., 6, 942 (2011); https://doi.org/10.1097/JTO.0b013e31821528d3
  32. K. Bergethon, A.T. Shaw, S.-H.I. Ou, R. Katayama, C.M. Lovly, N.T. McDonald, P.P. Massion, C. Siwak-Tapp, A. Gonzalez, R. Fang, E.J. Mark, J.M. Batten, H. Chen, K.D. Wilner, E.L. Kwak, J.W. Clark, D.P. Carbone, H. Ji, J.A. Engelman, M. Mino-Kenudson, W. Pao and A.J. Iafrate, J. Clin. Oncol., 30, 863 (2012); https://doi.org/10.1200/JCO.2011.35.6345
  33. S.H.R. Sebastian, M.A. Al-Alshaikh, A.A. El-Emam, C.Y. Panicker, J. Zitko, M. Dolezal and C.V. Alsenoy, J. Mol. Struct., 1119, 188 (2016); https://doi.org/10.1016/j.molstruc.2016.04.088
  34. A. Ali, M. Asif, P. Alam, M.J. Alam, M.A. Sherwani, R.H. Khan and S. Ahmad and Shamsuzzaman, Bioorg. Chem., 73, 83 (2017); https://doi.org/10.1016/j.bioorg.2017.06.001
  35. M. Bavadi, K. Niknam and O. Shahraki, J. Mol. Struct., 1146, 242 (2017); https://doi.org/10.1016/j.molstruc.2017.06.003
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