Anti-proliferative activities of 4H-pyran derivatives synthesized from benzoylacetone

Abstract

ABSTRACT. Benzoylacetone (1) underwent a series of multi-component reactions with aromatic aldehydes and malononitrile or ethyl cyanoacetate to produce the pyran derivatives 4a-f. The latter compounds reacted with malononitrile or ethyl cyanoacetate to yield the condensation products 5a-m. On the other hand, the reaction of 4a-f with either the diazonium salts 6a-c yielded the arylhydrazone derivatives 7a-i. The multi-component reaction of (1) with aromatic adehydes and cyclohexan-1,3-dione produced the  pyran derivatives 9a-c. Compound 1 underwent the Gewald’s reactions with elemental sulfur and malononitrile or ethyl cyanacetate yielding the thiophene derivatives 10a,b. Evaluations of the  synthesized  products were carried out against some selected cancer cell lines and the most active compounds were further evaluated against the seventeen cancer cell lines classified according to the disease. Morphological changes of A549 cell line by the effect of compound 7k was studied using microenvironment of the lung tissue where an excellent results was obtained.

KEY WORDS: Benzoylacetone, Multi-component reactions, Pyran, Thiophene, Arylhydrazone, Cytotoxicity

Bull. Chem. Soc. Ethiop. 2023, 37(2), 405-425.                                                            

DOI: https://dx.doi.org/10.4314/bcse.v37i2.12