(S)-2-(3,4,5-trimethoxybenzamido)pentanedioic acid | 35455-36-8

• 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-(3,4,5-trimethoxybenzamido)pentanedioic acid
• 英文别名: (2S)-2-[(3,4,5-trimethoxybenzoyl)amino]pentanedioic acid
• CAS: 35455-36-8
• 化学式: C₁₅H₁₉NO₈
• 分子量: 341.318
• InChiKey: FPDPBXJHNNOSNX-VIFPVBQESA-N

物化性质

• 沸点：
  520.4±50.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-(3,4,5-trimethoxybenzamido)pentanedioic acid 在 乙酸酐 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (S)-2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetic acid
  参考文献：
  名称：

  Novel 3-galloylamido-N′-substituted-2,6-piperidinedione-N-acetamide peptidomimetics as metalloproteinase inhibitors

  摘要：

  Both of aminopeptidase N (APN) and matrix metalloproteinase (MMP) are essential metallopeptidases in the development of tumor invasion and angiogenesis. Novel potent peptidomimetic inhibitors, containing 3-galloylamido-N'-substituted-2, 6-piperidinedione-N-acetamide, have been designed and synthesized according to the conformational constraint strategy. The preliminary biological test showed that most of the compounds displayed high inhibitory activity against MMP-2 and low activity against APN except compounds 6 (IC50 = 3.1 mu M) and 41 (IC50 = 5.2 mu M) which exhibit similar potency to Bestatin (IC50 = 2.4 mu M). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.095
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 苯 为溶剂， 生成 (S)-2-(3,4,5-trimethoxybenzamido)pentanedioic acid
  参考文献：
  名称：

  Li, Xun; Xu, Wen-Fang, Journal of Chemical Research, 2005, # 2, p. 94 - 95

  摘要：

  DOI：

文献信息

• Novel cyclic-imide peptidomimetics as aminopeptidase N inhibitors. Design, chemistry and activity evaluation. Part I
  作者：Qianbin Li、Hao Fang、Xuejian Wang、Liping Hu、Wenfang Xu

  DOI：10.1016/j.ejmech.2009.07.022

  日期：2009.12

  A series of aminopeptidase inhibitors with cyclic-imide scaffold are described. The biological characterization for the piperidinedione analogues revealed that most compounds displayed high inhibitory activity against APN. Among which 4l and 6 showed potent inhibition against APN with the IC50 value of 5.2 μM and 3.1 μM, respectively. In addition, 6 also displayed good activity in HL-60 cell assay

  描述了具有环酰亚胺支架的一系列氨基肽酶抑制剂。哌啶二酮类似物的生物学特性表明，大多数化合物显示出对APN的高抑制活性。其中4l和6表现出对APN的有效抑制作用，IC 50值分别为5.2μM和3.1μM。此外，6在HL-60细胞测定和体内抗转移测定中也显示出良好的活性。这种有趣的活性特征还可以指导设计具有“单锌”活性位点的靶哺乳动物氨肽酶的新型特异性抑制剂。
• Novel aminopeptidase N inhibitors derived from antineoplaston AS2–5 (Part I)
  作者：Xun Li、Junli Wang、Jinpei Li、Jifeng Wu、Yonggang Li、Huawei Zhu、Ruifang Fan、Wenfang Xu

  DOI：10.1016/j.bmc.2009.02.063

  日期：2009.4

  Overexpression of zinc-dependent metalloproteinase, aminopeptidase N (APN/CD13), is considered to be involved in the process of tumor invasion and metastasis. Herein we describe the synthesis and in vitro enzymatic inhibition assay of antineoplaston AS2-5 scaffold peptidomimetic compounds. The results demonstrated that most of these L-iso-glutamine derivatives displayed selective inhibitory activity against APN as compared with MMP-2, with IC50 values in the micromole range. The structure-activity relationships were also briefly discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• US3959492A
  申请人：——

  公开号：US3959492A

  公开（公告）日：1976-05-25
• Li, Xun; Xu, Wen-Fang, Journal of Chemical Research, 2005, # 2, p. 94 - 95
  作者：Li, Xun、Xu, Wen-Fang

  DOI：——

  日期：——
• Novel 3-galloylamido-N′-substituted-2,6-piperidinedione-N-acetamide peptidomimetics as metalloproteinase inhibitors
  作者：Qianbin Li、Hao Fang、Wenfang Xu

  DOI：10.1016/j.bmcl.2006.12.095

  日期：2007.5

  Both of aminopeptidase N (APN) and matrix metalloproteinase (MMP) are essential metallopeptidases in the development of tumor invasion and angiogenesis. Novel potent peptidomimetic inhibitors, containing 3-galloylamido-N'-substituted-2, 6-piperidinedione-N-acetamide, have been designed and synthesized according to the conformational constraint strategy. The preliminary biological test showed that most of the compounds displayed high inhibitory activity against MMP-2 and low activity against APN except compounds 6 (IC50 = 3.1 mu M) and 41 (IC50 = 5.2 mu M) which exhibit similar potency to Bestatin (IC50 = 2.4 mu M). (c) 2007 Elsevier Ltd. All rights reserved.