Novel triazole bridged quinoline-anthracene derivatives: synthesis, characterization, molecular docking, evaluation of electronic and enzyme inhibitory properties

Abstract

Two novel quinoline-anthracene conjugates comprising styrylquinoline and anthracene moieties linked by triazole bridges were designed and synthesized in good yields. These molecules were determined for some metabolic enzymes activities. Results indicated that the synthetic molecules exhibited powerful inhibitory actions against all aims as compared to the control molecules. K-i values of novel compound QA-1 for hCA I, hCA II, AChE, and alpha-glycosidase enzymes were obtained of 20.18 +/- 2.46 mu M, 14.63 +/- 1.14 mu M, 71.48 +/- 7.76 nM, 401.35 +/- 36.84 nM, respectively. Both compounds showed promising candidate complexes for drug development with considerable in vitro different enzymes inhibitory activities. The binding conformations patterns and interaction of QA-1 and QA-2 compounds with alpha-glucosidase, acetycholinesterase, carbonic anhydrase-I and carbonic anhydrase-II enzymes were investigated through molecular docking profiles. The docking outputs are consistent with the Ki and IC50 values of novel compounds. Three dimensional geometries and electronic properties of the title compounds were obtained by the applicational computational approach at B3LYP/6-31++G(d,p) level of theory.