Benzenesulfonylation of Methyl α-D-Glucopyranoside: Synthesis, Characterization and Antibacterial Screening

Abstract

A novel series of benzenesulfonyl derivatives of methyl α-D-glucopyranoside (1) were synthesized by reacting benzenesulfonyl chloride in pyridine followed by direct acylation method to yield 6-O-benzenesulfonyl derivative (2). In order to obtain newer products for antibacterial evaluation studies, the 6-O-benzenesulfonyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-11) containing a wide variety of functionalities in a single molecular framework. All the synthesized compounds have been confirmed by IR, 1H NMR and elemental analysis. These newly synthesized compounds were screened for in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that the acylated products exhibit moderate to good antibacterial activities. It was interesting to observe that the selected compounds were more sensitive against Gram-Ve bacteria than that of the Gram-+Ve bacterial strains.