Design and synthesis of mono/bis isoxazoline and pyrroline pendant chromone derivatives-anti-cancer activity

Abstract

A simple and efficient route for the synthesis of a series of new mono/bis isoxazolines, and pyrroline linked chromone heterocyclic hybrids has been developed from 2-aminochromone via key intermediate mono and 2-(diallylamino)chromen-4-one. The intermediate subjected to the [1,3] dipolar cycloaddition with insitu generated nitrile oxides and ring-closing metathesis to generate the regio selective Isoxazolines and 3-pyrrolines. All the derivatives were screened for their anti-cancer activity (Cell viability), compared to the standard drug Imatinib. Compounds 13b and 13e, 14b and 14g showed good inhibition at 10 µM concentration.

Graphical Abstract

Keywords:

• 1,3-Dipolar cycloaddition
• 2-aminochromone
• anti-cancer activity
• mono/bis isoxazolines
• ring-closing metathesis

Acknowledgements

WE thank the HOD's Osmania University, Telangana University, and JNTU Hyderabad for the opportunity to pursue his Ph.D. Our sincere thanks to Dr. Mahendra Patel for providing infrastructural facilities to carry out the research work and we are also indebted to Raja Jayakumar and Dr. V. Janardana Rao for their continuous guidance and support.

Supporting information

Full experimental detail, ¹H, ¹³C NMR and HRMS spectra. This material can be found via the “Supplementary Content” section of this article’s webpage.