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-γ-lactone and D-gluconic acid-γ-lactone, separately. Acid catalyzed dehydrative cyclization of the acyclic benzimidazole C-nucleoside afforded the corresponding 2-(β-D-gulo-) and 2-(β-D-gluco-)furanosyl benzimidazole C-nucleoside analogs. The structure and the anomeric configuration of C-nucleoside analogs obtained were determined by periodate oxidation, 1H 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.
Keywords: Antibacterial biofilm; Antifouling property; Circular dichroism; Furanosyl benzimidazoles; Saccharide benzimidazoles.
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