Abstract

A three-component reaction for the synthesis of novel 3-heteroaryl-coumarin utilizing acetylcoumarin synthon under ultrasonic irradiation was developed using chitosan-grafted poly(vinylpyridine) as an eco-friendly catalyst. The process is a simple, facile, efficient procedure for the preparation of compounds displaying a thiazole ring linked to coumarin moiety. Moreover, all the products were evaluated for their anticancer activities against HEPG2-1. The results revealed that three new compounds showed promising anticancer activities.

Highlights

  • Today, the second cause of death in the world is cancer (Gomes et al, 2011)

  • Coumarin is a naturally occurring material as well as a versatile synthetic scaffold exhibiting a wide spectrum of biological impacts including potential anticancer activities (Vosooghi et al, 2010) such as seselin (Nishino et al, 1990), acronycin (Thakur et al, 2015), calanone (Emami and Dadashpour, 2015), and tephrosin (Lin et al, 2014)

  • In the light of the above findings and in continuation of our efforts to synthesize new antitumor compounds (Abbas et al, 2015; Gomha et al, 2015c; Dawood and Gomha, 2015; Gomha et al, 2016a; Gomha et al, 2016b; Gomha et al, 2017a; Gomha et al, 2017b; Tao et al, 2018; Gomha et al, 2021), the aim of the present work is to design and synthesize thiazoles and thiadiazoles linked to position 3 of coumarin as novel 3-azolylcoumarins as expected anticancer agents, utilizing sonication technique and using chitosan-grafted poly(vinylpyridine) as an eco-friendly catalyst

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Summary

Introduction

The second cause of death in the world is cancer (Gomes et al, 2011). Chemotherapy has become one of the important methods for cancer treatment. Coumarin derivatives have a tremendous ability to regulate a diverse range of cellular pathways that can be explored for their selective anticancer activities (Geisler et al, 2011; Saidu et al, 2012). The biological evaluations of coumarins revealed that the engrossment of innumerable pathways via coumarins acts as anticancer agents. They target a number of pathways in cancer like as kinase inhibition, cell cycle arrest, heat shock protein (HSP90) inhibition, angiogenesis inhibition, monocarboxylate transporters inhibition, antimitotic activity, carbonic anhydrase inhibition, telomerase inhibition, aromatase inhibition, and sulfatase inhibition (Ekowati et al, 2010; Li et al, 2010; Wang et al, 2011; Bhattarai et al, 2021)

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