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Pharmaceutical Chemistry Journal

, Volume 50, Issue 7, pp 443–450 | Cite as

Synthesis, Antimicrobial and In Silico EGFR Inhibitory Activity Evaluation of Sulfonylamino Pyrrolidine Derivatives

  • B. Santosh Kumar
  • A. Raghavendra Guru Prasad
  • P. Raveendra Reddy
  • L. K. Ravindranath
Article
  • 80 Downloads

A series of novel sulfonylamino pyrrolidine derivatives were synthesized, characterized and evaluated for their antimicrobial activity. All compounds exhibited moderate activity against the microorganisms tested. The compounds were evaluated in silico for their ability to inhibit epidermal growth factor receptor (EGFR). Docking in silico demonstrated that the sulfonylamino pyrrolidine derivatives represent a new class of EGFR inhibitors and bind at the ATP binding pocket of the tyrosine kinase domain of EGFR. The free energy of binding and inhibition constant (k i) of the docked compounds were evaluated.

Keywords

sulfonylamino pyrrolidine derivatives synthesis antimicrobial activity docking epidermal growth factor receptor (EGFR, 1XKK) 

Notes

Acknowledgments

The authors are thankful to Dr. K. Bhanuprash (Chief Scientist, CSIR-IICT, Hyderabad, Telangana, India) for his valuable advice during the course of the work.

References

  1. 1.
    L.Wei, B. Biplab, L. M. Katrina, et al., Bioorg. Med. Chem., 22, 406 – 418 (2014).CrossRefGoogle Scholar
  2. 2.
    T. D. Penning, N. S. Chandrakumar, B. B. Chen, et al., J. Med. Chem., 43, 721 – 735 (2000).CrossRefPubMedGoogle Scholar
  3. 3.
    B. Santosh Kumar, A. Raghvendra Guru Prasad, et al., Ann. Pharm. Franç. (Accepted for publication).Google Scholar
  4. 4.
    L. L. Christopher, J. H. Jeffrey, J. B. Richard, et al., Org. Lett., 5, 2473 – 2475 (2003).CrossRefGoogle Scholar
  5. 5.
    S. Bondock, W. Fadaly and M. A. Metwally, Eur. J. Med. Chem., 45, 3692 – 3701 (2010).CrossRefPubMedGoogle Scholar
  6. 6.
    D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, et al., Eur. J. Med. Chem., 44, 1396 – 1404 (2009).CrossRefPubMedGoogle Scholar
  7. 7.
    R. Romagnoli, Pier Giovanni Baraldi, C. Lopez-Cara, et al., Bioorg. Med. Chem. (Accepted for publication); http://www.sciencedirect.com/science/article/pii/S0968089613010249.
  8. 8.
    L. Zhang, P. Zhan, X. Chen, et al., Bioorg. Med. Chem., 22, 633 – 642 (2014).CrossRefPubMedGoogle Scholar
  9. 9.
    Z. Yong-Yong, G. Lin, Z. Xue-Chu, et al., Eur. J. Med. Chem., 54, 123 – 136 (2012).CrossRefGoogle Scholar
  10. 10.
    M. Sreedevi, A. Raghavendra Guru Prasad, Y. N. Spoorthy, et al., J. Appl. Pharm., 5, 805 – 811 (2013).Google Scholar
  11. 11.
    P. K. Ranjith, R. Pakkath, K. R. Haridas, et al., Eur. J. Med. Chem., 71, 354 – 365 (2014).CrossRefPubMedGoogle Scholar
  12. 12.
    S. Shinya, S. Yoshihito, A. Masakazu, et al., Eur. J. Med. Chem., 71, 250 – 258 (2014)CrossRefGoogle Scholar
  13. 13.
    J. Schlessinger, Science, 306, 1506 – 1507 (2004).CrossRefPubMedGoogle Scholar
  14. 14.
    N. E. Hynes and G. MacDonald, Cell Biol., 21,177 – 184 (2009).Google Scholar
  15. 15.
    M. Dastagiri Reddy, A. Raghavendra Guru Prasad, Y. N. Spoorthy, et al., Adv. Pharm. Bull., 3, 153 – 159 (2013).Google Scholar
  16. 16.
    D. V. Narayana Rao, A. Raghavendra Guru Prasad, Y. N. Spoorthy, et al., Ann. Pharm. Franç., 72, 51 – 58 (2014).Google Scholar
  17. 17.
    E. R. Wood, A. T. Truesdale, O. B. McDonald, et al., Cancer Res., 64, 6652 – 6659 (2004).CrossRefPubMedGoogle Scholar
  18. 18.
    I. Wiegand, K. Hilpert, and R. E. Hancock, Nature Protoc., 3, 163 – 175 (2008).CrossRefGoogle Scholar
  19. 19.
    Y. C. Joshi, S. Shalini, P. J. Kavita, et al., J. Korean Chem. Soc., 55, 630 – 643 (2011).Google Scholar
  20. 20.
    J. Baselga and S. D. Averbuch, Drugs, 60, 33 – 40 (2000).CrossRefPubMedGoogle Scholar
  21. 21.
    C. H. Yun, T. J. Boggon, Y. Li, et al., Cancer Cell, 11, 217 – 227 (2007).CrossRefPubMedPubMedCentralGoogle Scholar
  22. 22.
    J. Stamos, M. X. Sliwkowski and C. Eigenbrot, J. Biol. Chem., 277, 46265 – 46272 (2002).Google Scholar
  23. 23.
    D. W. Rusnak, K. Lackey, K. Affleck, et al., Mol. Cancer Ther., 1, 85 – 94 (2001).PubMedGoogle Scholar
  24. 24.
    H. Zhong, L. M. Tran, and J. L. Stang, J. Mol. Graph. Model., 28, 336 – 346 (2009).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • B. Santosh Kumar
    • 1
  • A. Raghavendra Guru Prasad
    • 2
  • P. Raveendra Reddy
    • 1
  • L. K. Ravindranath
    • 1
  1. 1.Sri Krishnadevaraya UniversityAnantapurIndia
  2. 2.Faculty of Science and Technology, ICFAI Foundation for Higher EducationHyderabadIndia

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