Exploring the Detailed Spectroscopic Characteristics, Chemical and Biological Activity of Three Pyrone Derivatives Using Experimental and Theoretical Tools

Abstract

Theoretical investigations of three pharmaceutically active pyrone derivatives, (E)-4-fluoro-N'-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide (FMB), (E)-3-((2-(5-fluoro-2-methylphenyl)hydrazono)methyl)-4H-chromen-4-one (MHC) and (E)-3-((2-(2-trifluoromethyl)phenyl)hydrazono)methyl)-4H-chromen-4-one (TPM) are reported. Molecular geometries, vibrational spectra, molecular electrostatic potential, and electronic properties were investigated using density functional theory. The frontier orbitals analysis gives charge transfer within the pyrones. In order to perform a better description of the FMOs the density of states was determined. The molecular electrostatic potential maps were calculated to provide information on the chemical reactivity of the molecule and also to describe the intermolecular interactions. The descriptors are compared with that of 4-pyrone and chromen-4-one molecules. All these studies including docking studies help a lot in determining the biological activities of pyrone derivatives. Activities of pyrone derivatives are compared with 5-fluorouracil and azathioprine (anti-tumor, anti-proliferative standards) and were found to be higher than reference ones.

Keywords:

• DFT
• Pyrone
• docking
• anti-tumor activity
• anti-proliferative activity

Acknowledgments

The authors express their gratitude to Princess Nourah bint Abdulrahman University Researchers Supporting Project Number (PNURSP2022R13), Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Author’s contributions

Conceptualization, Y.Sheena Mary, Y.Shyma Mary; Methodology, Y.Sheena Mary; Writing draft, review and editing, Jamelah S.Al-Otaibi, Y.Sheena Mary, Y.Shyma Mary.