Published January 1, 2022 | Version v1
Journal article Open

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

  • 1. Sakarya Univ, Fac Arts & Sci, Dept Chem, TR-54050 Sakarya, Turkey
  • 2. Recep Tayyip Erdogan Univ, Fac Arts & Sci, Dept Chem, TR-53100 Rize, Turkey
  • 3. Sakarya Univ, Fac Med, TR-54050 Sakarya, Turkey

Description

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.

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