Skip to main content
Log in

Design and Synthesis of Some New 1,4-Benzoxazine-Isoxazole Hybrids as In Vitro Anticancer Agents

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

Abstract

Synthesis of twelve novel regioselective 1,4-benzoxazine-isoxazole hybrids as in vitro anticancer agents via Cu(I) catalyzed one-pot reaction of various terminal alkynes with 3-(3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanal in benign aqueous t-butanol at room temperature is presented herein. Five products have demonstrated promising activity, among those the compound 6f demonstrates outstanding activity towards PC3, A549, MCF-7, and HeLa with IC50 values of 2.61, 3.34, 2.74, and 7.04 μM respectively.

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.

Institutional subscriptions

Fig. 1.
Scheme 1.
Scheme 2.

Similar content being viewed by others

REFERENCES

  1. Rajanarendar, E., Raju, S., Nagi Reddy, M., Rama Krishna, S., Hari Kiran, L., Ram Narasimha Reddy, A., and Narasimha Reddy, Y., Eur. J. Med. Chem., 2012, vol. 50, p. 274. https://doi.org/10.1016/j.ejmech.2012.02.004

    Article  CAS  PubMed  Google Scholar 

  2. Srinivas, B., Vani, V., Prasad Rao, Ch., Vijay Kumar, P., Rama Krishna, K., and David Krupadanam, G.L., Bioorg. Med. Chem., 2017, vol. 27, p. 4314. https://doi.org/10.1016/j.bmcl.2017.08.033

  3. Yong, J.P., Lu, C.Z., and Wu, X., Anti-Cancer Agents Med. Chem., 2015, vol. 15,p. 131.

  4. Guiza1, F.M., Duarte, Y.B., Mendez Sanchez, S.C., and Romero Bohorquez, A.R., Med. Chem. Res., 2019, vol. 28, p. 1182. https://doi.org/10.1007/s00044-019-02363-z

  5. Naresh Kumar, R., Jitender Dev, G., Ravikumar, N., Krishna Swaroop, D., Debanjan, B., Bharath, G., Narsaiah, B., Nishant Jain, S., and Gangagni Rao, A., Bioorg. Med. Chem., 2016, vol. 26, p. 2927. https://doi.org/10.1016/j.bmcl.2016.04.038

  6. Rajitha, B., Vijayacharan, G., Jyothsna Devi, P., Rajashaker, B., Vijayacharan, G., Lingaiah, N., Sowjanya, P., and Nishant, J., Eur. J. Med. Chem., 2014, vol. 89, p. 138. https://doi.org/10.1016/j.ejmech.2014.10.051

    Article  CAS  Google Scholar 

  7. Narsimha, S., Kumara Swamy, B., Satheesh Kumar, N., Ramesh, G., Narasimha Reddy, Y., and Vasudeva Reedy, N., RSC Adv., 2016, vol. 6, p. 74332. https://doi.org/10.1039/C6RA12285J

  8. Miles, D.H., Petrovna, K.O., Naser, S., Yurjevich, S.S., Goun, E.A., Michailovich, S.V., US Patent 6649610, 2003.

  9. Hori, M., Watanabe, I., Ohtaka, H., Harada, K., Maruo, J., and Morita, T., Kanebo Ltd., EP Patent 0719766, 2000.

  10. Bhuniya, D., Das, S.K., Madhavan, G.R., Iqbal, J., and Chakrabarti, R., WO Patent 03033481, 2003.

  11. Burton, G.A., Hillmann, M., Hoelscher, P., Jaroch, S., Mcdonald, F. M., Rehwinkel, H., and Sulzle, D., WO Patent 017173, 2000.

  12. Burton, G.A., Hillmann, M., Hoelscher, P., Jaroch, S., Jautelat, R., Mcdonald, F.M., Rehwinkel, H., and Sulzle, D., WO Patent 081324, 2001.

  13. Huang, X. and Cheng-Chu, C., Communications, 1984, p. 851.

  14. Hansen, T. V., Wu, P., Valery., and Fokin, V., J. Org. Chem., 2005, vol. 70, p. 7761. https://doi.org/10.1021/jo050163b

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to B. Saritha or B. B. V. Sailaja.

Ethics declarations

This article does not contain any studies involving animals or human participants performed by any of the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Benarjee, V., Saritha, B. & Sailaja, B.B.V. Design and Synthesis of Some New 1,4-Benzoxazine-Isoxazole Hybrids as In Vitro Anticancer Agents. Russ J Gen Chem 91, 1783–1788 (2021). https://doi.org/10.1134/S1070363221090255

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221090255

Keywords:

Navigation