Synthesis, characterization, and biological activity evaluation of 4,6-dihydropyrano[3,2-c]isochromene-3-carbonitrile as anticancer agents

Abstract

Herein, a series of new 2-amino-4,6-dihydropyrano[3,2-c]isochromene-3-carbonitrile derivatives (4a-o) have been synthesized by one-pot three component reaction of 4-hydroxyisocoumarin, various aromatic aldehydes, and malononitrile in the presence of triethylamine in EtOH at reflux conditions. All the newly synthesized compounds were characterized using standard spectroscopic techniques (FT-IR, ¹H and ¹³C NMR) and elemental analysis. The cytotoxicity of the synthesized compounds was determined by MTT assay on one normal (3T3) and two cancer cell lines (A549 and MCF-7). It was revealed that some of these compounds (4b, 4f, and 4j) are toxic especially for MCF-7 cell line and can be considered as lead compounds for further investigation. Howevere, the other compounds had low cytotoxicity and can be suitable candidates for other pharmacological effects such as antibacterial, antifungal, antiviral, etc.