Skip to main content
SpringerLink
Log in

Design, Synthesis, and Anticancer Evaluation of 2-{3-{4-[(5-Aryl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}isoxazol-5-yl}-N-(3,4,5-trimethylphenyl)thiazol-4-amine Derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of new 2-{3-{4-[(5-aryl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}isoxazol-5-yl}-N-(3,4,5-tri-methylphenyl)thiazol-4-amine derivatives is synthesized, and the structures of products are confirmed by 1H and 13C NMR, and mass spectra. The new compounds are tested for their anticancer activity against human cancer cell lines: MCF-7 (breast), A549 (lung), Du-145 (prostate), and MDA MB-231 (breast) by using MTT assay and etoposide as a standard reference. All compounds demonstrate good to moderate activity on all cell lines.

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

Similar content being viewed by others

References

  1. Mayhoub, A.S., Khaliq, M., and Botting, C., Bioorg. Med. Chem., 2011, vol. 19, p. 3845. doi https://doi.org/10.1016/j.bmc.2011.04.041

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Jalilian, A.R., Sattari, S., Bineshmarvasti, M., Shafiee, A., and Daneshtalab, M., Arch. Pharm. Med. Chem., 2000, vol. 333, p. 347.doi https://doi.org/10.1002/1521-4184(200010)333:10%3C347::AID-ARDP347%3E3.0.CO;2-6

    Article  CAS  Google Scholar 

  3. Liu, C.L., Li, L., and Li, Z.M., Bioorg. Med. Chem., 2004, vol. 12, p. 2825. doi https://doi.org/10.1016/j.bmc.2004.03.050

    Article  CAS  PubMed  Google Scholar 

  4. Hutchinson, I., Chua, M.S., Browne, H.L., Trapani, V., Bradshaw, T.D., Westwell, A. D., and Stevens, M.F.G., J. Med. Chem., 2001, vol. 44, p. 1446. doi https://doi.org/10.1021/jm001104n

    Article  CAS  PubMed  Google Scholar 

  5. Dawood, K.M., Gawad, H.A., Rageb, E.A., Ellithey, M., and Mohamed, H.A., Bioorg. Med. Chem., 2006, vol. 14, p. 3672. doi https://doi.org/10.1016/j.bmc.2006.01.033

    Article  CAS  PubMed  Google Scholar 

  6. Vicini, P., Geronikaki, A., Anastasia, K., Incerti, M., and Zani, F., Bioorg. Med. Chem., 2006, vol. 14, p. 3859. doi https://doi.org/10.1016/j.bmc.2006.01.043

    Article  CAS  PubMed  Google Scholar 

  7. Kumar, A., Rajput, C.S., and Bhati, S.K., Bioorg. Med. Chem., 2007, vol. 15, p. 3089. doi https://doi.org/10.1016/j.bmc.2007.01.042

    Article  CAS  PubMed  Google Scholar 

  8. Shiradkar, M.R., Murahari, K.K., Gangadasu, H.R., Suresh, T., Kalyan, C.A., Panchal, D., Kaur, R., Burange, P., Ghogare, J., Mokalec, V., and Raut, M., Bioorg. Med. Chem., 2007, vol. 15, p. 3997. doi https://doi.org/10.1016/j.bmc.2007.04.003

    Article  CAS  PubMed  Google Scholar 

  9. Cohen, A., Verhaeghe, P., Crozet, M.D., Hutter, S., Rathelot, P., Vanelle, P., and Azas, N., Eur. J. Med. Chem., 2012, vol. 55, p. 315.doi https://doi.org/10.1016/j.ejmech.2012.07.034

    Article  CAS  PubMed  Google Scholar 

  10. Shih, M.H., and Ying, K.F., Bioorg. Med. Chem., 2004, vol. 12, p. 4633.doi https://doi.org/10.1016/j.bmc.2004.06.033

    Article  CAS  PubMed  Google Scholar 

  11. Abruzzese, E., Breccia, M., and Latagliata, R., Bio. Drugs, 2014, vol. 28, p. 17. doi https://doi.org/10.1007/s40259-013-0056-z

    CAS  Google Scholar 

  12. Pace, A., and Pierro, P., Org. Biomol. Chem., 2009, vol. 7, p. 4337. doi https://doi.org/10.1039/B908937C

    Article  CAS  PubMed  Google Scholar 

  13. Pace A., Buscemi, S., and Vivona, N., Org. Prep. Proced. Int., 2005, vol. 37, p. 447. doi https://doi.org/10.1080/00304940509354978

    Article  CAS  Google Scholar 

  14. Zhang, H.Z., Kasibhatla, S., and Kuemmerle, J., J. Med. Chem., 2005, vol. 48, p. 5215. doi https://doi.org/10.1021/jm050292k

    Article  CAS  PubMed  Google Scholar 

  15. Axel, K. and Jürgen, E., Pharmaceutical Substances: Syntheses, Patents, Applications, Thieme Chemistry, Stuttgart, Germany, 2001.

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Acharya Nagarjuna University, Nagarjuna Nagar, Andhra Pradesh, 522510, India

    T. Yakantham & R. R. Raju

  2. Department of Chemistry, University College of Engineering (Autonomous), Jawaharlal Nehru Technological University, Kakinada, 533003, Andhra Pradesh, India

    R. Sreenivasulu

Authors
  1. T. Yakantham
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Sreenivasulu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. R. Raju
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to R. R. Raju.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yakantham, T., Sreenivasulu, R. & Raju, R.R. Design, Synthesis, and Anticancer Evaluation of 2-{3-{4-[(5-Aryl-1,2,4-oxadiazol-3-yl)methoxy]phenyl}isoxazol-5-yl}-N-(3,4,5-trimethylphenyl)thiazol-4-amine Derivatives. Russ J Gen Chem 89, 1485–1490 (2019). https://doi.org/10.1134/S1070363219070181

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219070181

Keywords

Search

Navigation