Synthesis, quantum chemical computation, molecular docking analysis and biological activity of chlorophenylthiazolylnaphthylmethanone as dendrodoine analogs

Abstract

A series of chlorophenylthiazolylnaphthylmethanone derivatives have been synthesized and found to possess a wide spectrum of biological activities. Chlorophenylthiazolylnaphthylmethanone has been synthesized and characterized by elemental analysis IR, ¹H and ¹³C NMR and mass spectral data. Quantum chemical computation and vibrational spectral analysis of chlorophenylthiazolylnaphthylmethanone have been carried out using DFT level B3LYP with 6-31G basis set. Electric dipole moment (µ) values have been computed by utilizing ab initio and DFT quantum mechanical calculations. The energy gap is an indicator of chemical reactivity, kinetic stability and polarizability. The novel compounds show very good antioxidant and anticancer activity. Docking studies have been performed for target molecules using the molecular docking software. The antioxidant activity of chlorophenylthiazolylnaphthylmethanone has been analyzed using the DPPH radical scavenging assay. Among the studied compounds, (4-chlorophenyl-2-diethylaminothiazol-5-yl-2-naphthyl)methanone 2b is highly active on the SKMEL cell line.