Versatile Synthesis of rac- and meso-Hydroxymethyl Cyclohexenoids Containing Phenyl Groups: alpha-/beta-Glucosidase Activities, Inhibition Kinetics and Molecular Docking Studies


Sevmezler S., Col S., EMİRİK M. , Ceylan D., BARAN A.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol.2022, no.13, 2022 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2022 Issue: 13
  • Publication Date: 2022
  • Doi Number: 10.1002/ejoc.202200165
  • Title of Journal : EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Keywords: Docking studies, Hydroxymethyl cyclohexane, Inhibition kinetics, Structure-activity relationships, Synthesis design, COST-EFFECTIVE CATALYST, DRUG SYNTHESIS BIODS, STEREOSELECTIVE-SYNTHESIS, NORBORNYL ROUTE, EFFICIENT SYNTHESIS, MALEIC-ANHYDRIDE, BETA-GLUCOSIDASE, SULFAMIC ACID, CARBA-SUGARS, DERIVATIVES

Abstract

The effective strategy has been developed to synthesize a series of monophenyl and diphenyl carbasugar analogues, from the cycloadduct reaction of furan and maleic anhydride, containing halogen groups based on the conduritol scaffold. The strategy mainly consists of reduction, esterification, bromination, formation of new double bond and replacement of bromine with phenyl by Suzuki coupling reaction. New phenyl-substituted carbasugars were obtained by cleavage of the oxo bridge and subsequent hydrolysis of the esters. The structures of the target compounds were defined using different chemical methods. In vitro inhibitory activity studies, kinetic and molecular docking studies were performed against alpha-, beta-glucosidase enzymes for the final compounds.