6-(4'-azido-4'-deoxy-β-D-rhamnopyranosylamno)-4-chloro-5-nitropyrimidine | 245749-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(4'-azido-4'-deoxy-β-D-rhamnopyranosylamno)-4-chloro-5-nitropyrimidine
• CAS: 245749-52-4
• 化学式: C₁₀H₁₂ClN₇O₅
• 分子量: 345.702
• InChiKey: SLNHALTXDDJJAK-MYOXCZOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  179.4
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-(4'-azido-4'-deoxy-β-D-rhamnopyranosylamno)-4-chloro-5-nitropyrimidine 在 ammonium hydroxide 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 47.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2
• 作为产物：
  描述：

  4-deoxy-4-azido-D-rhamnopyranose 在 ammonium hydroxide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 6-(4'-azido-4'-deoxy-β-D-rhamnopyranosylamno)-4-chloro-5-nitropyrimidine
  参考文献：
  名称：

  Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin—is the mode of action by modification of N-linked glycoproteins?

  摘要：

  The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl alpha-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a containing an L-rhamnose fragment is shown to be highly cytotoxic towards human myeloma cells with an IC50=120 nM, whereas the D-(-)-enantiomer 2b, based on a D-mannose structure, shows no significant cytotoxicity. The analogue 16, in which the nucleotide base fragment has been replaced by a simple methoxy group, has no cytotoxicity. Initial studies towards clarifying the mechanism of anti-cancer action of spicamycin analogues are reported. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00240-2