S. Vaseghi, S. Emami, Mohamad Shokerzadeh
Jun 1, 2021
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Influential Citations
2
Citations
Quality indicators
Journal
Journal of Molecular Structure
Abstract
Abstract ((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, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The obtained data were compared with theoretical FT-IR, 1H NMR, 13C 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. The IC50 value for compound 3 against HepG2 (cancer cell line) and BEAS-2B (normal cell line) is 26.04 and 35.63 µg/mL that show moderate anticancer activity, however, its toxicity in comparison with 3-acetyl-4-hydroxycoumarin against HepG2 is higher.