A series of new methyl 6-deoxy-6-[N'-alkyl/aryl-N''-(benzothiazol-2-yl)]guanidino-alpha-D-glucopyranosides were obtained from the reaction of an alkyl/aryl amine in the presence of HgCl2 and sugar-thiourea derivatives, followed by the removal of protecting groups. The sugar-thiourea derivatives were obtained from the treatment of 2-aminobenzothiazole derivatives with methyl 2,3,4-tri-O-acetyl-6-deoxy-6-isothiocyanato-alpha-D-glucopyranoside in dry pyridine. Some of the synthesized guanidines displayed anti-influenza activity.
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Synthesis and bioactivity of novel methyl 6-deoxy-6-(N'-alkyl/aryl-N''-benzothiazol-2-yl)guanidino-alpha-D-glucopyranosides.
Carbohydr Res
March 2008
College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, PR China.
A series of new methyl 6-deoxy-6-[N'-alkyl/aryl-N''-(benzothiazol-2-yl)]guanidino-alpha-D-glucopyranosides were obtained from the reaction of an alkyl/aryl amine in the presence of HgCl2 and sugar-thiourea derivatives, followed by the removal of protecting groups. The sugar-thiourea derivatives were obtained from the treatment of 2-aminobenzothiazole derivatives with methyl 2,3,4-tri-O-acetyl-6-deoxy-6-isothiocyanato-alpha-D-glucopyranoside in dry pyridine. Some of the synthesized guanidines displayed anti-influenza activity.
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