Regioselective synthesis, characterization, and antimicrobial activities of some new monosaccharide derivatives.

ABSTRACT: A regioselective acylation series of methyl ?-D-glucopyranoside (1), methyl 3-O-benzoyl-4,6-O-benzylidene-?-D-mannopyranoside (1A), and methyl 4,6-O-benzylidene-2-O-(3,5-dinitrobenzoyl)-?-D-mannopyranoside (1B) has been carried out by the direct acylation method and afforded the 2,6-di-O-glucopyranoside and 2 or 3-O-mannopyranoside derivatives in an excellent yield. In order to obtain newer products, the 2,6-di-O-glucopyranoside derivative was further transformed to a series of 3,4-di-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated on the basis of IR, (1)H-NMR, (13)C-NMR, (13)C-DEPT spectral data, and elemental analysis. These synthesized derivatives were screened for in vitro antimicrobial activities against ten human pathogenic and five phytopathogenic microorganisms. A number of test compounds showed remarkable antimicrobial activity comparable to, and in some cases even higher than, the standard antibiotics employed. It was observed that methyl 3,4-di-O-(3-chlorobenzoyl)-2,6-di-O-hexanoyl-?-D-glucopyranoside (8) exhibited a varied range of MIC from 12.5 ?g/disc to 25 ?g/disc by the disk diffusion method and 1000 ?g/mL to 1250 ?g/mL by the broth macrodilution method.

SUBMITTER: Kawsar SM 

PROVIDER: S-EPMC3951222 | biostudies-literature | 2014 Jan-Mar

REPOSITORIES: biostudies-literature