Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Abstract

A novel regioselective benzenesulphonylation and N-acetylsulfanilylation series of methyl α-D-glucopyranoside derivative (1) has been carried out by direct method and afforded the 6-O-benzenesulfonyl derivative (2) and 6-O-N-acetylsulfanilyl derivative (7) in an excellent yields. In order to obtain newer products, the 6-O-glucopyranoside derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-6 and 8-11) containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated with the aid of FTIR, H-NMR spectroscopy and elemental analysis. All the synthesized compounds were also tested for their antibacterial activity against some human pathogenic bacterial microorganisms. For comparative studies, antibacterial activity of standard antibiotics, ampicillin was also carried out against these microorganisms. The study revealed that the acylated products exhibit moderate to good antimicrobial activities. It was interesting to observe that the selected compounds were more sensitive against gram-negative bacteria than that of the gram-positive bacterial strains. We carried out the antibacterial activities of the tested chemicals in vitro. In vivo screening studies of the tested compounds showing promising results will be the subject of our future investigation.