(2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(dimethylcarbamate) | 1374854-20-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(dimethylcarbamate)
• CAS: 1374854-20-2
• 化学式: C₅₅H₅₄N₂O₁₂
• 分子量: 935.04
• InChiKey: PPJQCCUXCVBYKD-JPPFXEPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  69.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  144.67
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(dimethylcarbamate) 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 以84%的产率得到C₂₇H₃₀N₂O₁₂
  参考文献：
  名称：

  Analogs of the RSK inhibitor SL0101: Optimization of in vitro biological stability

  摘要：

  The Ser/Thr protein kinase, RSK, is important in the etiology of tumor progression including invasion and motility. The natural product kaempferol-3-O-(3",4"-di-O-acetyl-alpha-L-rhamnopyranoside), called SL0101, is a highly specific RSK inhibitor. Acylation of the rhamnose moiety is necessary for high affinity binding and selectivity. However, the acetyl groups can be cleaved by esterases, which accounts for the poor in vitro biological stability of SL0101. To address this problem a series of analogs containing acetyl group replacements were synthesized and their in vitro stability evaluated. Monosubstituted carbamate analogs of SL0101 showed improved in vitro biological stability while maintaining specificity for RSK. These results should facilitate the development of RSK inhibitors derived from SL0101 as anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.033
• 作为产物：
  描述：

  4',5,7-tri-O-benzyl-kaempferol 3-O-(2''-O-benzyl-α-L-rhamnopyranoside) 、 二甲氨基甲酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.58h， 以69%的产率得到(2S,3S,4R,5R,6S)-5-(benzyloxy)-6-((5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)-2-methyltetrahydro-2H-pyran-3,4-diyl bis(dimethylcarbamate)
  参考文献：
  名称：

  Analogs of the RSK inhibitor SL0101: Optimization of in vitro biological stability

  摘要：

  The Ser/Thr protein kinase, RSK, is important in the etiology of tumor progression including invasion and motility. The natural product kaempferol-3-O-(3",4"-di-O-acetyl-alpha-L-rhamnopyranoside), called SL0101, is a highly specific RSK inhibitor. Acylation of the rhamnose moiety is necessary for high affinity binding and selectivity. However, the acetyl groups can be cleaved by esterases, which accounts for the poor in vitro biological stability of SL0101. To address this problem a series of analogs containing acetyl group replacements were synthesized and their in vitro stability evaluated. Monosubstituted carbamate analogs of SL0101 showed improved in vitro biological stability while maintaining specificity for RSK. These results should facilitate the development of RSK inhibitors derived from SL0101 as anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.033