(S)-methyl 2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetate | 942123-90-2

• 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)-methyl 2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetate
• 英文别名: methyl 2-[(3S)-2,6-dioxo-3-[(3,4,5-trimethoxybenzoyl)amino]piperidin-1-yl]acetate
• CAS: 942123-90-2
• 化学式: C₁₈H₂₂N₂O₈
• 分子量: 394.381
• InChiKey: WGCNWTXUEJFXAN-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetate 在 氢氧化钾 、 羟胺 作用下， 以 甲醇 为溶剂， 以60%的产率得到(S)-N-(1-(2-(hydroxyamino)-2-oxoethyl)-2,6-dioxopiperidin-3-yl)-3,4,5-trimethoxybenzamide
  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：

  (S)-N-(2,6-dioxo-tetrahydro-2H-pyran-3-yl)-3,4,5-trimethoxybenzamide 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (S)-methyl 2-(2,6-dioxo-3-(3,4,5-trimethoxybenzamido)piperidin-1-yl)acetate
  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

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 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.