Advertisement

Russian Journal of General Chemistry

, Volume 88, Issue 10, pp 2183–2189 | Cite as

Design, Synthesis, and Anticancer Evaluation of Tetrazole-Fused Benzoxazole Derivatives as Tubulin Binding Agents

  • P. RavikumarEmail author
  • G. S. B. Raolji
  • K. Venkata Sastry
  • S. Kalidasu
  • T. Balaaraju
Article
  • 14 Downloads

Abstract

A novel series of tetrazole fused benzoxazole derivatives 9a9j are synthesized, and their structures are characterized by 1H and 13C NMR, and mass spectra. The compounds 9a, 9b, 9g, 9h, and 9j demonstrate the highest activity. The compounds 9b and 9g exhibit good anticancer activity, in particular against MCF7, Hop62, and A-549 cell lines with the range of GI50 values from <0.1 to 4.56 μM. Molecular docking study is carried out for the compounds 9a9j, according to which the compound 9b forms one hydrogen bond with THR766 with the highest docking score (–7.33). This indicates that 9b is effeciently binging to tubulin site.

Keywords

tetraxole benzoxazole cephalosporin anticancer activity molecular docking 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Sheng, C., Xu, H., Wang, W., Cao, Y., Dong, G., Wang, S., Che, X., Ji, H., Miao, Z., Yao, J., and Zhang, W., Eur. J. Med. Chem., 2010, vol. 45, p. 3531. doi 10.1016/j.ejmech.2010.03.007CrossRefGoogle Scholar
  2. 2.
    Klimesova, V., Koci, J., Waisser, K., Kaustova, J., and Mollmann, U., Eur. J. Med. Chem., 2009, vol. 44, p. 2286. doi 10.1016/j.ejmech.2008.06.027CrossRefGoogle Scholar
  3. 3.
    Liu, Y.K., Lou, D.J., Qian, J.Q., and Xu, Z.Y., J. Zhejiang. Univ. Sci., 2009, vol. 10, p. 472. doi 10.1631/jzus.B0820366CrossRefGoogle Scholar
  4. 4.
    Prudhomme, M., Guyot, J., and Jeminet, G., J. Antibiot., 1986, vol. 39, p. 934. doi 10.7164/antibiotics.39.934CrossRefGoogle Scholar
  5. 5.
    Srinivas, A., Vidyasagar, J., and Sarangapani, M., J. Chem. Pharm. Res., 2010, vol. 2, p.319.Google Scholar
  6. 6.
    Yildiz-Oren, I., Yalcin, I., Aki-Sener, E., and Ucarturk, N., Eur. J. Med. Chem., 2004, vol. 39, p. 291. doi 10.1016/j.ejmech.2003.11.014CrossRefGoogle Scholar
  7. 7.
    Turan-Zitoni, G., Demirayak, S., Ozdemir, A., Kaplancikli, Z.A., and Yildiz, M.T., Eur. J. Med Chem., 2004, vol. 39, p. 267. doi 10.1016/j.ejmech.2003.11.001CrossRefGoogle Scholar
  8. 8.
    Srinivas, A., Vidyasagar, J., Swathi, K., and Sarangapani, M., J. Chem. Pharm. Res., 2010, vol. 2, p.213.Google Scholar
  9. 9.
    Ueki, M., Shibata, K., and Taniguchi, M., J. Antibiot. 1998, vol. 51, p.883.CrossRefGoogle Scholar
  10. 10.
    Ueki, M. and Taniguchi, M., J. Antibiot., 1997, vol. 50, p. 788CrossRefGoogle Scholar
  11. 11.
    Diwakar, S.D., Bhagwat, S.S., Shingare, M.S., and Gill, C.H., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 4678. doi 10.1016/j.bmcl.2008.07.007CrossRefGoogle Scholar
  12. 12.
    Bertinaria, M., Shaikh, M.A., and Buccellati, C., Chem. Med. Chem., 2012, vol. 7, p. 1647. doi 10.1002/cmdc.201200272CrossRefGoogle Scholar
  13. 13.
    Yeung, K.S., Qiu, Z., Yang, Z. Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 209. doi 10.1016/j.bmcl.2012.10.125CrossRefGoogle Scholar
  14. 14.
    Romagnoli, R., Baraldi, P.G., and Salvador, M.K., J. Med. Chem., 2012, vol. 55, p. 475. doi 10.1021/jm2013979CrossRefGoogle Scholar
  15. 15.
    Gundugola, A.S., Chandra, K.L., and Perchellet, E.M. Bioorg. Med. Chem. Lett.., 2010, vol. 20, p. 3920. doi 10.1016/j.bmcl.2010.05.012CrossRefGoogle Scholar
  16. 16.
    Luo, Y.P., Gong, Q., Chen, Q., and Yang, G.F., Chin. J. Org. Chem., 2008, vol. 28, p. 1561.Google Scholar
  17. 17.
    Trecant, C., Dlubala, A., and George, P., Eur. J. Med. Chem., 2011, vol. 46, p. 4035. doi 10.1016/j.ejmech.2011.05.076CrossRefGoogle Scholar
  18. 18.
    Scheffler, R.J., Colmer, S., Tynan, H., Demain, A.L., and Gullo, V.P., Appl. Microbiol. Biotechnol., 2013, vol. 97, p. 969. doi 10.1007/s00253-012-4609-8CrossRefGoogle Scholar
  19. 19.
    Lee, P.Y., Chang, W.N., Lu, C.H., Lin, M.W., Cheng, B.C., Chien, C.C., Chang, C., and Chang, H.W., Antimicrob. Agents Chemother., 2003, vol. 51, p. 957. doi 10.1093/jac/dkg158CrossRefGoogle Scholar
  20. 20.
    Balaraju, T., Kumar, A., Bal, C., Chattopadhyay, D., Jena, N., Bal, N.C., and Sharon, A., Struct. Chem., 2013, vol. 24, p. 1499.CrossRefGoogle Scholar
  21. 21.
    Thiyagarajan, A., Salim, M.T., Balaraju, T., Bal, C., Baba, M., and Sharon, A., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 7742. doi 10.1016/j.bmcl.2012.09.072CrossRefGoogle Scholar
  22. 22.
    Kasula, M., Balaraju, T., Toyama, M., Thiyagarajan, A., Bal, C., Baba, M., and Sharon, A., Chem. Med. Chem., 2013, vol. 8, p. 1673. doi 10.1002/cmdc.201300277Google Scholar
  23. 23.
    Genheden, S. and Ryde, U., Exp. Opinion Drug Disc., 2015, vol. 10, p. 449. doi 10.1517/17460441.2015.1032936CrossRefGoogle Scholar
  24. 24.
    Li, J., Abel, R., Zhu, K., Cao, Y., Zhao, S., and Friesner, R.A., Proteins, 2011, vol. 79, p. 2794. doi 10.1002/prot.23106CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • P. Ravikumar
    • 1
    • 2
    Email author
  • G. S. B. Raolji
    • 2
  • K. Venkata Sastry
    • 3
  • S. Kalidasu
    • 1
    • 2
  • T. Balaaraju
    • 4
  1. 1.Department of ChemistryJNT UniversityHyderabadIndia
  2. 2.GVK Biosciences Private Limited, Nacharam, IDA MallapurHyderabadIndia
  3. 3.CMR College of Pharmacy, MedchalHyderabadIndia
  4. 4.Department of Chemistry, School of ScienceGitam UniversityHyderabadIndia

Personalised recommendations