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Vol. 27 No. 8 (2015): Vol 27 Issue 8

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Synthesis and Antibacterial Activity of 1,5-Disubstituted Indolin-2-one Derivatives Containing Sulfonamides

https://doi.org/10.14233/ajchem.2015.18329
Qiu-Xian Liang
College of Life Science, Sichuan University, Chengdu 610064, P.R. China
Ling Liao
Department of Pathogenic Biology, School of Biomedical Science, Chengdu Medical College, Chengdu 610083, P.R. China
Juan Luo
Faculty of Chemistry, Sichuan University, Chengdu 610065, P.R. China
Shuai Pu
Faculty of Chemistry, Sichuan University, Chengdu 610065, P.R. China
Yu-Liang Wang
College of Life Science, Sichuan University, Chengdu 610064, P.R. China; Faculty of Chemistry, Sichuan University, Chengdu 610065, P.R. China
Tian Chen
Department of Pathogenic Biology, School of Biomedical Science, Chengdu Medical College, Chengdu 610083, P.R. China

Corresponding Author(s) : Yu-Liang Wang

chemwang2008@163.com

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8

Abstract

A series of novel 1,5-disubstituted indolin-2-one derivatives containing sulfonamides as potential antibacterial agent were synthesized and the antibacterial activity was preliminary evaluated against two Gram-positive bacteria S. aureus ATCC26112, S. aureus SC and Gram-negative bacteria P. vulgaris in vitro. The results indicated that most of the target compounds exhibited promising antibacterial potency. Compounds 7b, 7d and 8b showed notable antimicrobial activity with corresponding inhibition zone (IZ = 19 mm, 21 mm and 23.5 mm, respectively) at the concentration of 100 μg/mL against S. aureus ATCC26112.

Keywords

1 5-Disubstituted Indolin-2-one Sulfonamides Synthesis Antibacterial
Liang, Q.-X., Liao, L., Luo, J., Pu, S., Wang, Y.-L., & Chen, T. (2015). Synthesis and Antibacterial Activity of 1,5-Disubstituted Indolin-2-one Derivatives Containing Sulfonamides. Asian Journal of Chemistry, 27(8), 2959–2963. https://doi.org/10.14233/ajchem.2015.18329
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References
  1. J.S. Shi, J.X. Yu, X.P. Chen and R.X. Xu, Acta Pharmacol. Sin., 24, 97 (2003).
  2. A. Jossang, P. Jossang, H.A. Hadi, T. Sevenet and B. Bodo, J. Org. Chem., 56, 6527 (1991); doi:10.1021/jo00023a016.
  3. I.G. Otterness, T.J. Carty and L.D. Loose, in eds.: A.J. Lewis, N.S. Doherty and N.R. Ackerman, Therapeutic Approaches to Inflammatory Diseases, Elsevier Science, New York (1989).
  4. V.V. Vintonyak, K. Warburg, H. Kruse, S. Grimme, K. Hübel, D. Rauh and H. Waldmann, Angew. Chem. Int. Ed., 49, 5902 (2010); doi:10.1002/anie.201002138.
  5. A.L. Davis, D.R. Smith and T.J. McCord, J. Med. Chem., 16, 1043 (1973); doi:10.1021/jm00267a020.
  6. G. Kumari, M. Nutan, M. Modi, S.K. Gupta and R.K. Singh, Eur. J. Med. Chem., 46, 1181 (2011); doi:10.1016/j.ejmech.2011.01.037.
  7. H. Li, X. Zhang, J. Tan, L. Chen, H. Liu, X. Luo, X. Shen, L. Lin, K. Chen, J. Ding and H. Jiang, Acta Pharmacol. Sin., 28, 140 (2007); doi:10.1111/j.1745-7254.2007.00473.x.
  8. W.D. Blackburn, H.M. Prupas, J.C. Silverfield, J.E. Poiley, J.R. Caldwell, R.L. Collins, M.J. Miller, D.H. Sikes, H. Kaplan, R. Fleischmann, C.D. Scoville, J.E. Rutstein, E.R. Hurd, J.S. Louie, A.D. Bankhurst, A.L. Weaver, A.I. Sebba, D.J. Appelrouth, N.P. Hudson, G.V. Gordon, R.D. Gordon, C.L. Ludivico, M.C. Austin, K.M. Sanders, P.T. Schuette, R.A. Moidel, A.R. Kraska, N. Ting, W.R. Shanahan and L.D. Loose, Arthritis Rheum., 38, 1447 (1995); doi:10.1002/art.1780381011.
  9. M. Mohammadi, G. McMahon and L. Sun, Science, 276, 955 (1997); doi:10.1126/science.276.5314.955.
  10. L. Sun, N. Tran, F. Tang, H. App, P. Hirth, G. McMahon and C. Tang, J. Med. Chem., 41, 2588 (1998); doi:10.1021/jm980123i.
  11. A.D. Laird, P. Vajkoczy, L.K. Shawver, A. Thurnher, C. Liang, M. Mohammadi and J.M. Cherrington, Cancer Res., 60, 4152 (2000).
  12. X. Wang, P. Le, C. Liang, J. Chan, D. Kiewlich, T. Miller, D. Harris, L. Sun, A. Rice, S. Vasile, R.A. Blake, A.R. Howlett, N. Patel, G. McMahon and K.E. Lipson, Mol. Cancer Ther., 2, 1085 (2003).
  13. R.A. Blake, M.A. Broome, X. Liu, J. Wu, M. Gishizky, L. Sun and S.A. Courtneidge, Mol. Cell. Biol., 20, 9018 (2000); doi:10.1128/MCB.20.23.9018-9027.2000.
  14. G. Kiran, G. Rajyalakshmi, B. Baburao, J.V. Rao and M. Sarangapani, Pharmacologyonline, 1, 542 (2009).
  15. G. Kiran, R.R. Rajyalakshmi, J.V. Rao and M. Sarangapani, J. Pharm. Res., 2, 388 (2009).
  16. D. Lee, S.A. Long, J.L. Adams, G. Chan, K.S. Vaidya and T.A. Francis, J. Biol. Chem., 275, 16007 (2000); doi:10.1074/jbc.275.21.16007.
  17. D. Lee, S.A. Long, J.H. Murray, J.L. Adams, M.E. Nuttall, D.P. Nadeau, K. Kikly, J.D. Winkler, C.-M. Sung, M.D. Ryan, M.A. Levy, P.M. Keller and W.E. DeWolf, J. Med. Chem., 44, 2015 (2001); doi:10.1021/jm0100537.
  18. W. Chu, J. Zhang, C. Zeng, J. Rothfuss, Z. Tu, Y. Chu, D.E. Reichert, M.J. Welch and R.H. Mach, J. Med. Chem., 48, 7637 (2005); doi:10.1021/jm0506625.
  19. W. Chu, J. Rothfuss, A. d'Avignon, C. Zeng, D. Zhou, R.S. Hotchkiss and R.H. Mach, J. Med. Chem., 50, 3751 (2007); doi:10.1021/jm070506t.
  20. W. Chu, J. Rothfuss, D. Zhou and R.H. Mach, Bioorg. Med. Chem. Lett., 21, 2192 (2011); doi:10.1016/j.bmcl.2011.03.015.
  21. P. Limpachayaporn, M. Schäfers, O. Schober, K. Kopka and G. Haufe, Bioorg. Med. Chem., 21, 2025 (2013); doi:10.1016/j.bmc.2013.01.011.
  22. P. Limpachayaporn, S. Wagner, K. Kopka, S. Hermann, M. Schäfers and G. Haufe, J. Med. Chem., 56, 4509 (2013); doi:10.1021/jm400257a.
  23. K. Kopka, A. Faust, P. Keul, S. Wagner, H.J. Breyholz, C. Höltke, O. Schober, M. Schäfers and B. Levkau, J. Med. Chem., 49, 6704 (2006); doi:10.1021/jm051217c.
  24. G. Smith, M. Glaser, M. Perumal, Q.D. Nguyen, B. Shan, E. Arstad and E.O. Aboagye, J. Med. Chem., 51, 8057 (2008); doi:10.1021/jm801107u.
  25. Y. Jiang and T.V. Hansen, Bioorg. Med. Chem. Lett., 21, 1626 (2011); doi:10.1016/j.bmcl.2011.01.110.
  26. Y.S. Lai, Y.H. Zhang and Y.Z. Li, Chin. J. Med. Chem., 13, 99 (2003).
  27. G. Tacconi, P.P. Righetti and G. Desimoni, J. Prakt. Chem., 315, 339 (1973); doi:10.1002/prac.19733150221.
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