Studies on saccharide benzimidazoles: 2-(beta-D-gulofuranosyl)benzimidazole and 2-(beta-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency

摘要

A series of acyclic 2-(D-gulo-) and 2-(D-gluco-)benzimidazole C-nucloside analogs have been prepared by condensation of o-phenylenediamine dihydrochloride derivatives with D-gulonic acid-gamma-lactone and D-gluconic acid-gamma-lactone, separately. Acid catalyzed dehydrative cyclization of the acyclic benzimidazole C-nucleoside afforded the corresponding 2-(beta-D-gulo-) and 2-(beta-D-gluco-)furanosyl benzimidazole C-nucleoside analogs. The structure and the anomeric configuration of C-nucleoside analogs obtained were determined by periodate oxidation, H-1 NMR, UV and circular dichroism (CD) spectroscopy. The antifouling property of C-nucleoside analogs has been studied using antibacterial biofilm test. 2-(D-gulo-) and 2-(D-gluco-)benzimidazole analogs were useful for inhibiting marine bacterial growth and did not cause any bad effect to the surrounding seawater.