1-デオキシ-1-ウレイドグルクロン酸関連化合物の合成研究 (第2報)

1-(3-Arylmethyleneaminothioureido)-1-deoxy-β-D-glucopyranuronic AcidおよびそのAmideの合成ならびに抗結核作用

抄録

Reaction of hydrazine with methyl 1-deoxy-1-isocyanato-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (I) in dioxane affords methyl 1-(3-aminothioureido)-1-deoxy-2, 3, 4-tri-O-acetyl-β-D-glucopyranuronate (II) which undergoes condensation with aromatic aldehydes to form the corresponding thiosemicarbazone derivatives (III). Treatment of (III) with dilute alkali or ammonia in methanol gives 1-(3-arylmethyleneaminothioureido)-1-deoxy-β-D-glucopyranuronic acids (V) or -uronamides (VI). Treatment of (II) with ammonia in methanol affords 1-(3-aminothioureido)-1-deoxy-β-D-glucopyran-uronamide (IV) whose condensation with aldehyde also gives (VI). Infrared spectra of (II), (II′)-(VI) exhibit thioureido absorption at around 1530cm^-1 and of (II) and (III) the asymmetric stretching vibration of C-O-C in the β-pyranose ring at around 1080cm^-1. In vitro antituberculosis action of (V) and (VI) was not any better than the aromatic aldehyde thiosemicarbazones used as the control.