Synthesis, spectroscopic (FT-IR, FT-Raman), solvent effects (absorption, fluorescence), electronic and biological evaluation of 7-methyl-4-(4-methyl-2-nitro-phenoxymethyl)-2H-chromen-2-one

Abstract

In this work, the 7-methyl-4-(4-methyl-2-nitro-phenoxymethyl)-2H-chromen-2-one (7MMNPC) is synthesized by the reaction of 7-methyl-4-bromomethylcoumarin with 4-methyl-2-nitro-phenol in presence of anhydrous potassium carbonate using dry acetone as solvent. Then, it is characterized by several spectral and photophysical properties. Most of the analyses have been investigated by experimental and theoretical methods. Initially, molecular structural characteristics have been obtained by optimized structure with DFT/B3LYP/ 6–311++G (d, p) basis set and compared with reported experimental data. The fundamental vibrational modes of the molecule are fully assigned and examined by observed FT-IR and FT-Raman data and compared with harmonic vibrational wavenumbers obtained by the DFT method. The photophysical properties analyses have been conducted to measure the dipole moments in the ground (μg) and excited (μe) state. The Frontier Molecular Orbital (FMO) analysis depicts that energy gap of HOMO- LUMO is 4.04 eV. Molecular Electrostatic Potential (MEP) analyses are carried out to investigate the molecule's electronic properties. The ADMET and pharmacokinetic parameters are calculated to determine whether the synthesized compound has the potential to be a drug. The toxicological properties of the compound have been investigated. The molecular docking study is conducted to determine the molecule's good degree of inhibition against non-small cell lung cancer (NSCLC).