(S)-6-benzoylamino-2-[(2,3-dibenzyloxybenzoyl)amino]hexanoic acid methyl ester | 1147012-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-6-benzoylamino-2-[(2,3-dibenzyloxybenzoyl)amino]hexanoic acid methyl ester
• CAS: 1147012-02-9
• 化学式: C₃₅H₃₆N₂O₆
• 分子量: 580.681
• InChiKey: YRIFSHQJOBZOAE-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-6-benzoylamino-2-[(2,3-dibenzyloxybenzoyl)amino]hexanoic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以43%的产率得到(S)-6-benzoylamino-2-[(2,3-dihydroxybenzoyl)amino]hexanoic acid methyl ester
  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：

  2,3-双(苄氧基)苯甲酸 、 Nε-benzoyl-L-lysine methyl ester 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36%的产率得到(S)-6-benzoylamino-2-[(2,3-dibenzyloxybenzoyl)amino]hexanoic acid methyl ester
  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