Synthesis, characterization, crystal structure, anti-cancer activities, and computational study of a novel thiophenylchromane

Abstract

• ((thiophen-2-ylmethyl)amino)ethylidene)chromane-2,4-dione was synthesized. • The theoretical and experimental data confirmed each other. • The structure of ligand was studied with crystallography. • The ligand displayed moderate anticancer properties. ((thiophen-2-ylmethyl)amino)ethylidene)chromane-2,4-dione ( 3 ) was synthesized using 1:1 ratio of 3-acetyl-4-hydroxycoumarin and thiophen-2-ylmethanamine. The main goal of this study was to determine the crystalline structure of compound 3 , mainly to investigate if the dominant chemical form is imine or enamine. Therefore, it was synthesized and characterized with FT-IR, 1 H NMR, 13 C NMR, mass spectroscopy, and elemental analysis. The obtained data were compared with theoretical FT-IR, 1 H NMR, 13 C NMR calculated with density functional theory (DFT), which confirmed that there is a good correlation between them. The single-crystal X-ray structure of compound 3 was also solved using the crystallography data which confirmed that compound 3 is an enamine rather than an imine. Compound 3 showed significant inhibitory effect against MCF-7, HepG2, U87-MG, SKOV3, MDA-MB231, BEAS-2B, and L929 cell lines (IC 50 values < 50 µg/mL). In particular, the IC 50 values of compound 3 against HepG2 (cancer cell line) and BEAS-2B (normal cell line) were 26.04 and 35.63 µg/mL, respectively.