Skip to main content
SpringerLink
Log in

Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors

  • Letters to the Editor
  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of novel indole derivatives were synthesized as potent inhibitors for the vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase. Among those, compound 10b demonstrated the highest growth inhibition rate of 66.7% against the VEGFR-2 tyrosine kinase at 10 μM which indicates that indole-benzothiazole might be the favorable structure. The binding mode of compound 10b with VEGFR-2 tyrosine kinase was evaluated by molecular docking.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Herdman, C.A., Devkota, L., Lin, C.M., Niu, H., Strecker, T.E., Lopez, R., Li, L., George, C.S., Tanpure, R.P. and Hamel, E., Bioorgan. Med. Chem., 2015, vol. 23, p. 7497. doi 10.1016/j.bmc.2015.10.012

    Article  CAS  Google Scholar 

  2. Siemann, D.W., Chaplin, D.J., and Horsman, M.R., Cancer, 2005, vol. 104, p. 216. doi 10.1002/cncr.21120

    Article  Google Scholar 

  3. Bold, G., Schnell, C., Furet, P., McSheehy, P., Brüggen, J., Jürgen, M., Manley, P.W., Drueckes, P., Burglin, M., and Dürler, U.J., Med. Chem., 2016, vol. 59, p. 132. doi 10.1021/acs.jmedchem.5b01582

    Article  CAS  Google Scholar 

  4. Kang, C.M., Liu, D.Q., Wang, X.Y., Yu, R.L., and Lv, Y.T., J. Mol. Graph. Model., 2015, vol. 59, p. 130. doi 10.1016/j.jmgm.2015.04.011

    Article  CAS  Google Scholar 

  5. La, L., Ps, S., and Wg, S.-S., Cell, 1991, vol. 64, p. 327. doi 10.1016/0092-8674(91)90642-C

    Article  Google Scholar 

  6. Parangi, S., O'Reilly, M., Christofori, G., Holmgren, L., Grosfeld, J., Folkman, J., and Hanahan, D., Proc. Natl. Acad. Sci., 1996, vol. 93, p. 2002.

    Article  CAS  Google Scholar 

  7. Folkman, J., Ann. Surg., 1972, vol. 175, p. 409.

    Article  CAS  Google Scholar 

  8. Hahn, O. and Stadler, W., Curr. Opin. Oncol., 2006, vol. 18, p. 615. doi 10.1097/01.cco.0000245316.82391.52

    Article  CAS  Google Scholar 

  9. Druker, B.J., Tamura, S., Buchdunger, E., Ohno, S., Segal, G.M., Fanning, S., Zimmermann, J., and Lydon, N.B., Nat. Med., 1996, vol. 2, p. 561. doi 10.1038/nm0596-561

    Article  CAS  Google Scholar 

  10. Barker, A.J., Gibson, K.H., Grundy, W., Godfrey, A.A., Barlow, J.J., Healy, M P., Woodburn, J.R., Ashton, S.E., Curry, B.J., and Scarlett, L., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 1911. doi 10.1002/chin.200146147

    Article  CAS  Google Scholar 

  11. Feng, S., Yuan, T., Chen-Yu, T., Fei, Z., and Xin-Yan, W., J. Org. Chem., 2015, vol. 80, p. 8122. doi 10.1021/acs.joc.5b01223

    Article  Google Scholar 

  12. El-Sawy, E.R., Abo-Salem, H.M., Mahmoud, K., Zarie, E.S., El-Metwally, A.M., and Mandour, A. H., Int. J. Pharm. Pharm. Sci., 2015, vol. 7, p. 377.

    CAS  Google Scholar 

  13. El-Sawy, E., Mandour, A., Yahya, S., Abo-Salem, H., and Ebaid, M., Egypt. Pharm. J., 2015, vol. 14, p. 15. doi 10.4103/1687-4315.154695

    Article  Google Scholar 

  14. Madadi, N.R., Penthala, N.R., Janganati, V., and Crooks, P.A., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 601. doi 10.1016/j.bmcl.2013.12.013

    Article  CAS  Google Scholar 

  15. Papaetis, D.G.S. and Syrigos, K.N., Biodrugs, 2009, vol. 23, p. 377. doi 10.2165/11318860-000000000-00000

    Article  CAS  Google Scholar 

  16. Sekwon Jang, M.D., Chaoyi Zheng, M.S., Tsai, H.T., Fu, A.Z., Barac, A., Atkins, M.B., Freedman, A.N., Lori Minasian, M.D., and Potosky, A.L., Cancer, 2016, vol. 122, p. 124. doi 10.1002/cncr.29728

    Article  Google Scholar 

  17. Jiang, F. and Kang, C., Chemistry, 2015, vol. 78, p. 378. doi 10.14159/j.cnki.0441-3776.2015.04.017

    CAS  Google Scholar 

  18. Jing, X., Zhu, Q., Xu, F., Ren, X., Li, D., and Yan, C., Cheminform, 2006, vol. 36, p. 2597. doi 10.1002/chin.200707098

    CAS  Google Scholar 

  19. Siegart, W.R. and Day, A.R., J. Am. Chem. Soc., 1957, vol. 79, p. 4391. doi 10.1021/ja01573a041

    Article  CAS  Google Scholar 

  20. Melzer, M.S., J. Org. Chem., 1962, vol. 27, p. 496. doi 10.1021/jo01049a038

    Article  CAS  Google Scholar 

  21. Süs, O. and Möller, K., Eur. J. Org. Chem., 1955, vol. 593, p. 91. doi 10.1002/jlac.19555930202

    Google Scholar 

  22. Baiocchi, L. and Giannangeli, M., J. Heterocyclic Chem., 1988, vol. 25, p. 1905. doi 10.1002/jhet.5570250654

    Article  CAS  Google Scholar 

  23. Venkatesh, P. and Pandeya, S.N., Int. J. Chemtech. Res., 2009, vol. 1, p. 1354.

    CAS  Google Scholar 

  24. Henry, D.W., and Leete, E., J. Am. Chem. Soc., 1957, vol. 79, p.5254. doi 10.1021/ja01576a051

    Article  CAS  Google Scholar 

  25. Borgne, M.L., Marchand, P., Duflos, M., Delevoye-Seiller, B., Piessard-Robert, S., Baut, G.L., Hartmann, R.W., and Palzer, M., Archiv. Der. Pharmazie. 1997, vol. 330, p. 141. doi 10.1002/chin.199742155

    Article  Google Scholar 

  26. Li, Y. and Tan, R., Liaoning. Chem. Ind., 1999, vol. 28, p. 97.

    Google Scholar 

  27. Skolnik, H., Miller, J.G., and Day, A.R., J. Am. Chem. Soc., 2002, vol. 65, p. 1858. doi 10.1021/ja01250a020

    Article  Google Scholar 

  28. Shen, X.A., Mod. Chem. Ind., 2008, vol. 28, p. 43. doi 10.16606/j.cnki.issn0253-4320.2008.06.002

    CAS  Google Scholar 

  29. Ge, Y., Wu, Y., Xue, Z., and Zhou, M., Chem. Ind. Times., 2004, vol. 18, p. 24. doi 10.16597/j.cnki.issn.1002-154x.2004.07.008

    CAS  Google Scholar 

  30. Lee, K.Y., Lee, H.S., and Kim, J.N., Cheminform, 2007, vol. 28, p. 333. doi 10.1002/chin.200728113

    CAS  Google Scholar 

  31. Ferro, S., Grazia, S.D., Luca, L.D., Barreca, M.L., Debyser, Z., and Chimirri, A., Heterocycles, 2009, vol. 78, p. 947. doi 10.3987/com-08-11573

    Article  CAS  Google Scholar 

  32. Trott, O. and Olson, A.J., J. Comput. Chem., 2010, vol. 31, p. 455. doi 10.1002/jcc.21334

    CAS  Google Scholar 

  33. Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., and Ferrin, T.E., J. Comput. Chem., 2004, vol. 25, p. 1605. doi 10.1002/jcc.20084

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    C. Zhang, D. Xu, J. Wang & C. Kang

Authors
  1. C. Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. J. Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. C. Kang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to C. Kang.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, C., Xu, D., Wang, J. et al. Efficient Synthesis and Biological Activity of Novel Indole Derivatives as VEGFR-2 Tyrosine Kinase Inhibitors. Russ J Gen Chem 87, 3006–3016 (2017). https://doi.org/10.1134/S1070363217120465

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363217120465

Keywords

Search

Navigation