Synthesis and bioactivity of novel methyl 6-deoxy-6-(N'-alkyl/aryl-N''-benzothiazol-2-yl)guanidino-alpha-D-glucopyranosides.
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.
Liu
Yong-Hua
YH
College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046, PR China.
Cao
Ling-Hua
LH
D000478:Alkylation; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D052160:Benzothiazoles / Q000737:chemistry*; D002460:Cell Line; D018360:Crystallography, X-Ray; D004285:Dogs; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019791:Guanidine / Q000737:chemistry*; D009981:Influenza B virus / Q000187:drug effects; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry
D000998:Antiviral Agents; D052160:Benzothiazoles; D005960:Glucosides; D013890:Thiourea; D019791:Guanidine; D010100:Oxygen