Synthesis and comprehensive spectroscopic (X-ray, NMR, FTIR, UV–Vis), quantum chemical and molecular docking investigation of 3-acetyl-4‑hydroxy‑2-oxo-2H-chromen-7-yl acetate

Abstract

In the present study, the structural, spectroscopic (FT-IR, NMR, and UV–Vis) and electronic properties of newly synthesized 3-acetyl-4‑hydroxy‑2-oxo-2H-chromen-7-yl acetate (3AcHyC) were determined by experimental and theoretical methods. The structural parameters (bond lengths and angles) were calculated using the B3LYP-D3BJ/6–311++G(d,p) theoretical model and compared with the experimentally determined crystal structure of the investigated compound. Hirshfeld surfaces and fingerprint plots analysis were used to find and analyze the percentage of intermolecular interactions in the crystal structure of the investigated compound. The calculated FT-IR frequencies were determined from the same theoretical model and matched with experimental data. The NMR chemical shifts (1H and 13C) were recorded in the CDCl3 solution and compared with theoretically determined spectra. The UV–Vis absorption spectrum was analyzed and compared with the spectrum calculated by Time-Dependent Density Functional Theory (TD-DFT). The obtained and compared spectroscopic data demonstrated that applied level theory reproduces well the experimental results. Furthermore, to examine the electronic structure of the studied molecule, the Natural Bond Orbitals (NBOs), the Quantum Theory of Atoms in Molecules (QTAIM), Non-linear Optical parameter (NLO), and Mapped Molecular Electrostatic Potential (MEP) surface analyses were also performed with the same level of theory. Furthermore, results of in silico molecular docking calculations, indicate the stability as well as favorable binding interactions between the investigated compound and the Tyrosyl DNA-Phosphodiesterase 1 (TDP1) active site. Also, the results indicate that the investigated compound is a favorable precursor in the synthesis of new coumarin derivatives with potentially significant biological and pharmacological properties.