1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-amino-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]diazepin-4-one | 475568-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-amino-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]diazepin-4-one
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(6-amino-4,8-dioxo-7H-triazolo[4,5-e][1,3]diazepin-1-yl)oxan-2-yl]methyl acetate
• CAS: 475568-66-2
• 化学式: C₁₉H₂₂N₆O₁₁
• 分子量: 510.417
• InChiKey: RXRAWAPZGYYKAU-FRRILYKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.04
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  234.97
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-amino-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]diazepin-4-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以59%的产率得到6-amino-1-(β-D-glucopyranosyl)-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]diazepin-4-one
  参考文献：
  名称：

  NEW GLYCOSYL-(CARBOXAMIDE)-1,2,3-TRIAZOLE-N-NUCLEOSIDES: SYNTHESIS AND ANTITUMOR ACTIVITY

  摘要：

  A series of potential bioactive compounds, 1-glucopyranosyl-1,2,3-triazole-4,5-dimethylcarboxylate, 1-glucopyranosyl-1,2,3-triazole-4,5-N-dicarbox-amide,-dialkyl-dicarboxamide-N-nucleosides and 6-amine-4H-1-(beta-D-glucopyranosyl)-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]-diazepin-4-one, were synthesized. Primary activity screening of the novel nucleosides showed poor or no anticancer activity against breast, lung and CNS tumors.

  DOI：

  10.1081/ncn-120006830
• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 120.5h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-amino-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]diazepin-4-one
  参考文献：
  名称：

  NEW GLYCOSYL-(CARBOXAMIDE)-1,2,3-TRIAZOLE-N-NUCLEOSIDES: SYNTHESIS AND ANTITUMOR ACTIVITY

  摘要：

  A series of potential bioactive compounds, 1-glucopyranosyl-1,2,3-triazole-4,5-dimethylcarboxylate, 1-glucopyranosyl-1,2,3-triazole-4,5-N-dicarbox-amide,-dialkyl-dicarboxamide-N-nucleosides and 6-amine-4H-1-(beta-D-glucopyranosyl)-8-hydroxy-1,2,3-triazolo[4,5-e][1,3]-diazepin-4-one, were synthesized. Primary activity screening of the novel nucleosides showed poor or no anticancer activity against breast, lung and CNS tumors.

  DOI：

  10.1081/ncn-120006830