Multicomponent reactions of cyanoacetanilide derivatives: Synthesis of coumarin and quinoline derivative and evaluations of their cytotoxicity

Abstract

In this study, several fused heterocyclic systems involving tetrahydrobenzopyrans 7a-i and tetrahydrobenzopyridines 9a-i were synthesized. The reactions proceed via a multicomponent reaction of different aromatic aldehydes, cyanoacetanilide derivatives, and cyclohexane-1,3-dione. All the produced compounds were tested for their anticancer activity by using six cancer cell lines such as A549, HT-29, MKN-45, U87MG, SMMC-7721 and H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. The results indicated that many synthesized derivatives were the most potent towards all the cancer cell lines used, six compounds 7e, 7f, 9b, 9d, 9e, and 9g   showed the highest potency. The results obtained in this work enhance further investigations in the future.

KEY WORDS: Multi-component reactions, Cyanoacetanilide, Pyran, Pyridine, Cytotoxicity

Bull. Chem. Soc. Ethiop. 2024, 38(3), 739-750.                                                            

DOI: https://dx.doi.org/10.4314/bcse.v38i3.15