Studies on saccharide benzimidazoles: 2-(ß-D-gulofuranosyl)benzimidazole and 2-(ß-D-glucofuranosyl)benzimidazole C-nucleoside analogs; synthesis, anomeric configuration and antifouling potency.
Carbohydr Res
; 496: 108073, 2020 Oct.
Article
em En
| MEDLINE
| ID: mdl-32818707
ABSTRACT
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-(ß-D-gulo-) and 2-(ß-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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Benzimidazóis
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Incrustação Biológica
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Antibacterianos
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Nucleosídeos
Idioma:
En
Revista:
Carbohydr Res
Ano de publicação:
2020
Tipo de documento:
Article