(S)-2,5-bis[(2,3-dibenzyloxybenzoyl)amino]pentanoic acid methyl ester

• 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)-2,5-bis[(2,3-dibenzyloxybenzoyl)amino]pentanoic acid methyl ester
• 英文别名: methyl (2S)-2,5-bis[[2,3-bis(phenylmethoxy)benzoyl]amino]pentanoate
• 化学式: C₄₈H₄₆N₂O₈
• 分子量: 778.902
• InChiKey: AXXCOKKERCWQPT-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2,5-bis[(2,3-dibenzyloxybenzoyl)amino]pentanoic acid methyl ester 在 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 以83%的产率得到(-)-2,3-dibenzyloxybenzoyl-L-Orn(2,3-dibenzyloxybenzoyl)-NH2
  参考文献：
  名称：

  Myxochelins B、C、D、E 和 F：一种模仿自然的强大铁载体的新结构原理

  摘要：

  描述了天然铁载体 myxochelin B (1S) 及其对映异构体 1R 的合成。1S 和 1R 用作合成新的六齿铁载体、粘螯素 C (7S) 和 CR (7R)、D (14S) 和 DR (14R)、E (19S) 和 (RS)-F (26R, S) 的前体)，具有 2,3-二羟基苯甲酸酯 (DHB) 配体和不对称 1,2,n-三氨基-n-烷烃的简单骨架。对于粘螯素 C、D、E 和 F，n 分别为 6（来自赖氨酸）、5（来自鸟氨酸）、4（来自天冬酰胺）和 7[来自 (±)-2-氨基庚二酸]。起始化合物中额外的氨基官能团是通过相应伯酰胺的脱水和随后在甲醇中硼化钴还原腈来提供的。所有新的铁载体为细菌提供三价铁离子，其效率取决于它们的链长和立体化学。

  DOI：

  10.1002/(sici)1099-0690(199803)1998:3<541::aid-ejoc541>3.0.co;2-a
• 作为产物：
  描述：

  2,3-双(苄氧基)苯甲酸 、 (S)-ornithine methyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 生成 (S)-2,5-bis[(2,3-dibenzyloxybenzoyl)amino]pentanoic 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

文献信息

• Myxochelins B, C, D, E and F: A New Structural Principle for Powerful Siderophores Imitating Nature
  作者：Horst-Dieter Ambrosi、Vera Hartmann、Daniel Pistorius、Rolf Reissbrodt、Wolfram Trowitzsch-Kienast

  DOI：10.1002/(sici)1099-0690(199803)1998:3<541::aid-ejoc541>3.0.co;2-a

  日期：1998.3

  The synthesis of the natural siderophore myxochelin B (1S) and its enantiomer 1R is described. 1S and 1R served as precursors for the synthesis of new hexadentate siderophores, the myxochelins C (7S) and CR (7R), D (14S) and DR (14R), E (19S) and (RS)-F (26R, S), with 2,3-dihydroxybenzoate (DHB) ligands and the simple backbones of asymmetric 1,2,n-triamino-n-alkanes. For the myxochelins C, D, E and

  描述了天然铁载体 myxochelin B (1S) 及其对映异构体 1R 的合成。1S 和 1R 用作合成新的六齿铁载体、粘螯素 C (7S) 和 CR (7R)、D (14S) 和 DR (14R)、E (19S) 和 (RS)-F (26R, S) 的前体)，具有 2,3-二羟基苯甲酸酯 (DHB) 配体和不对称 1,2,n-三氨基-n-烷烃的简单骨架。对于粘螯素 C、D、E 和 F，n 分别为 6（来自赖氨酸）、5（来自鸟氨酸）、4（来自天冬酰胺）和 7[来自 (±)-2-氨基庚二酸]。起始化合物中额外的氨基官能团是通过相应伯酰胺的脱水和随后在甲醇中硼化钴还原腈来提供的。所有新的铁载体为细菌提供三价铁离子，其效率取决于它们的链长和立体化学。
• Synthesis and evaluation of myxochelin analogues as antimetastatic agents
  作者：Satoshi Miyanaga、Hiroaki Sakurai、Ikuo Saiki、Hiroyasu Onaka、Yasuhiro Igarashi

  DOI：10.1016/j.bmc.2009.02.040

  日期：2009.4

  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.