New chalcone derivative, ethyl 2-(4-(3-(benzo[b]thiophen-2yl)acryloyl)phenoxy)acetate: synthesis, characterization, DFT study, enzyme inhibition activities and docking study

Compound I was characterized by proton and carbon-13 nuclear magnetic resonance (1H- and 13CNMR), fourier transform infrared (FTIR) and mass (LC-ESI-MS/MS) spectroscopic methods. Density Functional Theory (DFT) calculations for compound I were performed at B3LYP/6-311thornthornG(d,p) level. Optimized geometry, frontier molecular orbitals (HOMO; highest occupied molecular orbital; LUMO: lowest unoccupied molecular orbital), IR and NMR parameters of compound I were obtained. The evaluations reveal that the calculation results support the experimental results. The inhibition effects of compound I on cholinesterases and GST enzyme were investigated. Ki and inhibition concentration (IC50) values were calculated separately. Ki values of compound I were found for GST 14.19 +/- 2.15, for AChE 11.13 +/- 1.22 and for BChE 8.74 +/- 0.76 recpectively. The docking analysis of compound I supported the enzym inhibition activity exhibiting high inhibition constant and binding energy for three receptors. Compound I is strongly bound to AChE, huBChE and Glutathione S-transferase with binding energies - 11.24, -8.56 and -10.39 kcal/mol, respectively.

Automated summary

Compound I was characterized using proton and carbon-13 nuclear magnetic resonance, Fourier transform infrared, and mass spectroscopic methods. Density Functional Theory calculations were performed to obtain the molecular properties of compound I. The results showed that compound I exhibited inhibitory effects on cholinesterases and GST enzyme, and had high binding energies to three receptors.