(S)-2,6-bis[(2,3-dibenzyloxybenzoyl)amino]-N-benzyloxyhexanamide | 1147012-01-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2,6-bis[(2,3-dibenzyloxybenzoyl)amino]-N-benzyloxyhexanamide
• CAS: 1147012-01-8
• 化学式: C₅₅H₅₃N₃O₈
• 分子量: 884.041
• InChiKey: YMNMAVSUWZUFTI-DYVQZXGMSA-N

物化性质

• 密度：
  1.218±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  66.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  133.45
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (S)-2,6-bis[(2,3-dibenzyloxybenzoyl)amino]-N-benzyloxyhexanamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到(S)-2,6-bis[(2,3-dihydroxybenzoyl)amino]-N-hydroxyhexanamide
  参考文献：
  名称：

  Synthesis and evaluation of myxochelin analogues as antimetastatic agents

  摘要：

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.040
• 作为产物：
  描述：

  苄氧基胺盐酸盐 、 (S)-2,6-bis[(2,3-dibenzyloxybenzoyl)amino]hexanoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以67%的产率得到(S)-2,6-bis[(2,3-dibenzyloxybenzoyl)amino]-N-benzyloxyhexanamide
  参考文献：
  名称：

  Synthesis and evaluation of myxochelin analogues as antimetastatic agents

  摘要：

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.040