Synthesis and structure activity relationships of four series of novel 2-imino-2H-chromene-3(N-aryl)
carboxamides (V-VIII) have been described by bioisosteric replacement of usually present ketone at 2nd position of
coumarin with imine. Various substitutents are introduced on aryl and chromene ring of iminocoumarin to investigate
the effect of lipophilicity and electronic properties of substituents on cytotoxic activity against four human cancer cell
lines. Novel 2-imino-2H-chromene-3(N-aryl)carboxamides (V-VIII) were synthesized by the reaction of substituted 2-
cyanoacetamides with different salicyaldehydes in the presence of sodium acetate in glacial acetic acid. Compound
VIa showed potent activity against MCF-7 (IC50 = 8.5 μM), PC-3 (IC50 = 35.0 μM), A-549 (IC50 = 0.9 μM) and Caco-2
(IC50 = 9.9 μM) cell lines. The anticancer results revealed that most of the synthesized compounds showed equipotent
activity with the standard 5-fluorouracil and docetaxel on Caco-2 and MCF-7 cell lines, respectively.
Keywords: Coumarin, cytotoxicity, bioisosteric, carboxamides, MCF-7.
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