methyl (2S)-2-amino-6-(prop-2-enamido)hexanoate | 81504-08-7

• 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: methyl (2S)-2-amino-6-(prop-2-enamido)hexanoate
• 英文别名: N^ε-Acryloyl-L-lysin-methylester；methyl 2-amino-6-(prop-2-enoylamino)hexanoate
• CAS: 81504-08-7
• 化学式: C₁₀H₁₈N₂O₃
• 分子量: 214.265
• InChiKey: XVYUENQJTBQAOL-UHFFFAOYSA-N

物化性质

• 沸点：
  380.8±42.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.04
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  81.42
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-amino-6-(prop-2-enamido)hexanoate 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 benzyl N-[(2S)-1-(dimethylamino)-1-oxo-6-(prop-2-enoylamino)hexan-2-yl]carbamate
  参考文献：
  名称：

  SAR Development of Lysine-Based Irreversible Inhibitors of Transglutaminase 2 for Huntington's Disease

  摘要：

  We report a series of irreversible transglutaminase 2 inhibitors starting from a known lysine dipeptide bearing an acrylamide warhead. We established new SARs resulting in compounds demonstrating improved potency and better physical and calculated properties. Transglutaminase selectivity profiling and in vitro ADME properties of selected compounds are also reported.

  DOI：

  10.1021/ml300241m
• 作为产物：
  描述：

  6-Acryloylamino-2-tert-butoxycarbonylamino-hexanoic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2S)-2-amino-6-(prop-2-enamido)hexanoate
  参考文献：
  名称：

  Inhibition of angiogenesis by THAM-derived cotelomers endowed with thalidomide moieties

  摘要：

  The synthesis of a tris(hydroxymethyl)acrylamidomethane (THAM)-derived cotelomer endowed with thalidomide units and a preliminary assessment of its biological activity are described. 4-Carboxy thalidomide and 4-(N-acryloyl) lysine thalidomide derivatives were prepared. The polymerization of these compounds with THAM in the presence of octanethiol as transfer reagent provided a water-soluble telomer bearing several thalidomide units. The ability of this telomer to inhibit angiogenesis in a mouse model of corneal neovascularization was compared to 4-carboxy thalidomide and thalidomide. A significant inhibition in area of neovascularization stimulated by a bFGF pellet was observed only in the mice treated with the telomer. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.045