O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone | 206053-57-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2E)-2-(carbamothioylhydrazinylidene)ethoxy]oxan-2-yl]methyl acetate
• CAS: 206053-57-8
• 化学式: C₁₇H₂₅N₃O₁₀S
• 分子量: 463.466
• InChiKey: SBQKQCPJUNHJAM-WTNFTJOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  206
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以71%的产率得到O-(β-D-glucopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone
  参考文献：
  名称：

  Synthesis and SOD-Like Activity of Monosaccharide Derived Thiosemicarbazones

  摘要：

  The synthesis of new O-beta-D-glucopyranosyl- and O-beta-D-galactopyranosyl-2-hydroxyacetaldehyde thiosemicarbazones (5a,b) is reported. Oxidation of allyl glycoside 1 with KMnO4 followed by NaIO4 cleavage of the resulting diol 2 afforded aldehyde 3, which was then condensed with thiosemicarbazide and deprotected to give the target compounds (5a,b). Compounds 5a,b showed hydrolytic stability in neutral solution with half-life periods greater than 70 h. The SOD-mimetic activity was determined for the Cu(II) and Mn(II) complexes of 5a,b (IC50 = 0.2-0.8 mu M). This activity is higher by two orders of magnitude than copper (II) bisthiosemicarbazones. The ESR and UV-Vis data of Cu(II)-5a suggest a tetrahedral distortion of the coordination sphere around the central copper atom which could be the reason for their high SOD-mimetic activity.

  DOI：

  10.1080/07328309808002329
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 在 potassium permanganate 、 sodium periodate 、 苄基三乙基氯化铵 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 28.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-hydroxyacetaldehyde thiosemicarbazone
  参考文献：
  名称：

  Synthesis and SOD-Like Activity of Monosaccharide Derived Thiosemicarbazones

  摘要：

  The synthesis of new O-beta-D-glucopyranosyl- and O-beta-D-galactopyranosyl-2-hydroxyacetaldehyde thiosemicarbazones (5a,b) is reported. Oxidation of allyl glycoside 1 with KMnO4 followed by NaIO4 cleavage of the resulting diol 2 afforded aldehyde 3, which was then condensed with thiosemicarbazide and deprotected to give the target compounds (5a,b). Compounds 5a,b showed hydrolytic stability in neutral solution with half-life periods greater than 70 h. The SOD-mimetic activity was determined for the Cu(II) and Mn(II) complexes of 5a,b (IC50 = 0.2-0.8 mu M). This activity is higher by two orders of magnitude than copper (II) bisthiosemicarbazones. The ESR and UV-Vis data of Cu(II)-5a suggest a tetrahedral distortion of the coordination sphere around the central copper atom which could be the reason for their high SOD-mimetic activity.

  DOI：

  10.1080/07328309808002329