3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl bromide | 64605-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl bromide
• 英文别名: [(2S,3S,4S,6S)-3-acetyloxy-6-bromo-2-methyloxan-4-yl] acetate
• CAS: 64605-22-7
• 化学式: C₁₀H₁₅BrO₅
• 分子量: 295.13
• InChiKey: DCYXHMVVTCMQQC-RAWIJENESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  洋红霉素酮 、 3,4-di-O-acetyl-2,6-dideoxy-α-L-arabino-hexopyranosyl bromide 生成 2'-deoxy-L-fucopyranosylcarminomycinone
  参考文献：
  名称：

  EL, KHADEM, H. S.;SWARTZ, D. L.

  摘要：

  DOI：

文献信息

• ——
  作者：Sofia Mitaku、Alexios‐Léandros Skaltsounis、François Tillequin、Michel Koch、Yves Rolland、Alain Pierré、Ghanem Atassi

  DOI：10.1023/a:1016073700344

  日期：——

  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.
• FLORENT, J. C.;GENOT, A.;MONNERET, C., J. ANTIBIOTICS , 42,(1989) N2, C. 1823-1830
  作者：FLORENT, J. C.、GENOT, A.、MONNERET, C.

  DOI：——

  日期：——
• Skaltsounis, Alexios-Leandros; Mitaku, Sofia; Gaudel, Gilbert, Heterocycles, 1992, vol. 34, # 1, p. 121 - 128
  作者：Skaltsounis, Alexios-Leandros、Mitaku, Sofia、Gaudel, Gilbert、Tillequin, Francois、Koch, Michel

  DOI：——

  日期：——