Insulin-like, and insulin-antagonistic, carbohydrate derivatives. The synthesis of aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides.
A number of novel, aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides were synthesized for evaluation of insulin-like and insulin-antagonistic properties. The substituted-phenyl alpha-D-mannopyranosides were prepared by the general procedure of Helferich and Schmitz-Hillebrecht, the substituted-phenyl 1-thio-alpha-D-mannopyranosides by a method corresponding to the Michael synthesis of aromatic glycosides, and the aralkyl 1-thio-alpha-D-mannopyranosides by aralkylation of 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranose (15) and subsequent O-deacetylation. Compound 15 was obtained by basic cleavage of the amidino group in 2-S-(tetra-O-acetyl-alpha-D-mannopyranosyl)-2-thiopseudourea hydrobromide, the product of the reaction of tetra-O-acetyl-alpha-D-mannosyl bromide with thiourea. Benzyl 1-thio-beta-D-mannopyranoside, obtained by reaction of the sodium salt of 1-thio-beta-D-mannopyranose with alpha-bromotoluene, and benzyl 1-thio-alpha-L-mannopyranoside were also synthesized, in order to assess the stereospecificity of the biological activities measured.
D000818:Animals; D001681:Biological Assay; D006224:Cricetinae; D005260:Female; D005306:Fertilization / Q000187:drug effects; D006027:Glycosides / Q000138:chemical synthesis*; D007328:Insulin; D007329:Insulin Antagonists; D008264:Macrophages / Q000187:drug effects; D008362:Mannosides / Q000138:chemical synthesis* / Q000494:pharmacology; D008722:Methods; D051381:Rats; D013329:Structure-Activity Relationship; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000494:pharmacology
D006027:Glycosides; D007328:Insulin; D007329:Insulin Antagonists; D008362:Mannosides; D013865:Thioglycosides