1,2-Dihydroacronycin-2(R)-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside | 179678-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2-Dihydroacronycin-2(R)-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside
• CAS: 179678-64-9
• 化学式: C₂₆H₃₂N₂O₆
• 分子量: 468.55
• InChiKey: WULDTHDMBAKXFA-NPETZXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1,2-Dihydroacronycin-2(R)-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到(2R)-2-hydroxy-1,2-dihydroacronycine
  参考文献：
  名称：

  摘要：

  Purpose. Combination of the acronycine pharmacophore with various sugar units appeared of interest, since numerous anticancer agents possess a sugar moiety, which strongly influence both their bioavailability and their selective toxicity towards tumor cells.Methods. A series of 2-hydroxy-1,2-dihydroacronycine glycosides were synthetized, by condensation of the racemic aglycone with appropriate glycoside donors. Their effect on the inhibition of L1210 cell proliferation were evaluated.Results. Compounds 6a, 6b, 11a, 11b, and 12a, 12b, including a halogenated sugar moiety displayed activities of the same order of magnitude as acronycine itself. Compounds 7a, 7b, and Sa, 8b, bearing a 2,3,6-trideoxy-3-azido-L-lyxo- and L-arabino-hexopyranose unit respectively, were significantly more potent than acronycine in inhibiting cell proliferation.Conclusions. The activity of 2-hydroxy-1,2-dihydroacronycine glycosides seems to be related to the Lipophilicity of the sugar unit.

  DOI：

  10.1023/a:1016073700344
• 作为产物：
  描述：

  1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose 在 palladium on activated charcoal 氢气 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 1,2-Dihydroacronycin-2(R)-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  摘要：

  Purpose. Combination of the acronycine pharmacophore with various sugar units appeared of interest, since numerous anticancer agents possess a sugar moiety, which strongly influence both their bioavailability and their selective toxicity towards tumor cells.Methods. A series of 2-hydroxy-1,2-dihydroacronycine glycosides were synthetized, by condensation of the racemic aglycone with appropriate glycoside donors. Their effect on the inhibition of L1210 cell proliferation were evaluated.Results. Compounds 6a, 6b, 11a, 11b, and 12a, 12b, including a halogenated sugar moiety displayed activities of the same order of magnitude as acronycine itself. Compounds 7a, 7b, and Sa, 8b, bearing a 2,3,6-trideoxy-3-azido-L-lyxo- and L-arabino-hexopyranose unit respectively, were significantly more potent than acronycine in inhibiting cell proliferation.Conclusions. The activity of 2-hydroxy-1,2-dihydroacronycine glycosides seems to be related to the Lipophilicity of the sugar unit.

  DOI：

  10.1023/a:1016073700344