Skip to main content
Log in

Synthesis of Novel Amide-Functionalized Imidazo[1,2-a]pyrimidin-5(1H)-ones and Their Biological Evaluation as Anticancer Agents

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

Abstract

A series of novel amide-functionalized imidazo[1,2-a]pyrimidin-5(1H)-ones were synthesized by propargylation of the key intermediate 2-amino-6-(trifluoromethyl)pyrimidin-4(3H)-one, followed by cycliza­tion and amide functionalization. All synthesized compounds were evaluated for their anticancer activity against different human cancer cell lines, and most of them showed a good activity. In particular, pyrrolidine-derived imidazo[1,2-a]pyrimidine showed excellent anticancer activity against HeLa cell line.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Jemal, A., Siegel, R., Ward, E., Murray, T., and Xu, J., Ca-Cancer J. Clin., 2007, vol. 57, p. 43. https://doi.org/10.3322/canjclin.57.1.43

    Article  PubMed  Google Scholar 

  2. Mcintosh, H., Cochrane Library, 2001, vol. 4. https://doi.org/10.1002/14651858.CD000386

  3. Joffe, A.M., Farley, J.D., Linden, D., and Goldsand, G., Am. J. Med., 1989, vol. 87, p. 332. https://doi.org/10.1016/s0002-9343(89)80160-3

    Article  CAS  PubMed  Google Scholar 

  4. Cash, T.F., Br. J. Dermatol., 1999, vol. 141, p. 398. https://doi.org/10.1046/j.1365-2133.1999.03030.x

    Article  CAS  PubMed  Google Scholar 

  5. Petersen, E. and Schmidt, D.R., Expert Rev. Anti-Infect. Ther., 2003, vol. 1, p. 175. https://doi.org/10.1586/14787210.1.1.175

    Article  CAS  PubMed  Google Scholar 

  6. Dusza, H.P. and Albright, J.D., US Patent no. 5037980, 1991; Chem. Abstr., 1991, vol. 115, no. 256202q. https://patents.google.com/patent/US5037980?oq=us5037980

  7. Takayuki, O., Bharat, B., and Tomas, N., J. Heterocycl. Chem., 1983, vol. 20, p. 735. https://doi.org/10.1002/jhet.5570200345

    Article  Google Scholar 

  8. Köppe, H., Kummer, W., Stachle, H., and Stockhaus, K., FRG Patent Appl. no. 2234622, 1974; Chem. Abstr., 1974, vol. 80, no. 120993. https://patents.google.com/patent/DE2234622A1/en?oq=DE2234622+

  9. Stachle, H., Kummer, W., and Köppe, H., FRG Patent Appl. no. 3124718, 1983; Chem. Abstr., 1983, vol. 114, no. 126153. https://patents.google.com/patent/DE3124718A1/en?oq=DE3124718

  10. Stachle, H., Kummer, W., and Köppe, H., FRG Patent Appl. no. 2109524, 1972; Chem. Abstr., 1972, vol. 77, no. 164750. https://patents.google.com/patent/DE2109524A1/en?oq=DE2109524

  11. Tsuda, Y, Mishina, T., Obata, M., and Inui, J., EP Patent Appl. Pub. no. 0163240, 1985; Chem. Abstr., 1986, vol. 104, no. 186438. https://patents.google.com/patent/EP0163240A2/en?oq=EP0163240A2

  12. Freeman, C.G., Turner, J.V., and Ward, A.D., Aust. J. Chem., 1978, vol. 31, p. 179. https://doi.org/10.1071/CH9780179

    Article  CAS  Google Scholar 

  13. Saczewski, J., Brzozowski, Z., and Gdaniec, M., Tetra­hedron, 2005, vol. 61, p. 5303. https://doi.org/10.1016/j.tet.2005.03.063

    Article  CAS  Google Scholar 

  14. Nagender, P., Malla Reddy, G., Naresh Kumar, R., Chandrashekar Reddy, A., Lokka Reddy, V., Rajesh, P., Venkateswara Rao, J., and Narsaiah, B., Lett. Drug Des. Discovery, 2013, vol. 10, p. 865. https://doi.org/10.2174/1570180811310090010

    Article  CAS  Google Scholar 

  15. Nagender, P., Malla Reddy, G., Sambashiva Rao, P., Kurumurthy, C., Shanthana Rao, P., and Narsaiah, B., Chem. Lett., 2013, vol. 42, p. 1018. https://doi.org/10.1246/cl.130454

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to the department of research and development, Dr. JCR Bio-Sciences Private Limited, for the support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. Annareddygari.

Ethics declarations

The authors declare the absence of conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Annareddygari, S., Kasireddy, V. & Reddy, J. Synthesis of Novel Amide-Functionalized Imidazo[1,2-a]pyrimidin-5(1H)-ones and Their Biological Evaluation as Anticancer Agents. Russ J Org Chem 58, 412–418 (2022). https://doi.org/10.1134/S1070428022030216

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022030216

Keywords:

Navigation