2-ethyl-2-(3-phenyl-propionylamino)-butyric acid | 1070798-64-9

• 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: 2-ethyl-2-(3-phenyl-propionylamino)-butyric acid
• 英文别名: 2-Ethyl-2-(3-phenylpropanoylamino)butanoic acid；2-ethyl-2-(3-phenylpropanoylamino)butanoic acid
• CAS: 1070798-64-9
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: WFTHVWJDXLNNBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethyl-2-(3-phenyl-propionylamino)-butyric acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以98.69%的产率得到4,4-diethyl-2-phenethyl-4H-oxazol-5-one
  参考文献：
  名称：

  Synthesis and calpain inhibitory activity of peptidomimetic compounds with constrained amino acids at the P2 position

  摘要：

  The effect of incorporating alpha,alpha'-diethylglycine and alpha-aminocyclopentane carboxylic acid at the P-2 position of inhibitors on mu-calpain inhibition was studied. Compound 3 with alpha,alpha'-diethylglycine was over 20-fold more potent than 2 with alpha-aminocyclopentane carboxylic acid. Additionally, 3 was over 35-fold selective for mu-calpain compared to cathepsin B, while 2 was 3-fold selective for cathepsin B compared to mu-calpain. Thus, the conformation induced by the P2 residue influenced the activities of the compounds versus the closely related cysteine proteases, and suggests an approach to the discovery of selective mu-calpain inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.094
• 作为产物：
  描述：

  2-ethyl-2-(3-phenyl-propionylamino)-butyric acid methyl ester 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 36.0h， 以87%的产率得到2-ethyl-2-(3-phenyl-propionylamino)-butyric acid
  参考文献：
  名称：

  Synthesis and calpain inhibitory activity of peptidomimetic compounds with constrained amino acids at the P2 position

  摘要：

  The effect of incorporating alpha,alpha'-diethylglycine and alpha-aminocyclopentane carboxylic acid at the P-2 position of inhibitors on mu-calpain inhibition was studied. Compound 3 with alpha,alpha'-diethylglycine was over 20-fold more potent than 2 with alpha-aminocyclopentane carboxylic acid. Additionally, 3 was over 35-fold selective for mu-calpain compared to cathepsin B, while 2 was 3-fold selective for cathepsin B compared to mu-calpain. Thus, the conformation induced by the P2 residue influenced the activities of the compounds versus the closely related cysteine proteases, and suggests an approach to the discovery of selective mu-calpain inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.094

文献信息

• Synthesis and calpain inhibitory activity of peptidomimetic compounds with constrained amino acids at the P2 position
  作者：Isaac O. Donkor、Rajani Korukonda

  DOI：10.1016/j.bmcl.2008.07.094

  日期：2008.9

  The effect of incorporating alpha,alpha'-diethylglycine and alpha-aminocyclopentane carboxylic acid at the P-2 position of inhibitors on mu-calpain inhibition was studied. Compound 3 with alpha,alpha'-diethylglycine was over 20-fold more potent than 2 with alpha-aminocyclopentane carboxylic acid. Additionally, 3 was over 35-fold selective for mu-calpain compared to cathepsin B, while 2 was 3-fold selective for cathepsin B compared to mu-calpain. Thus, the conformation induced by the P2 residue influenced the activities of the compounds versus the closely related cysteine proteases, and suggests an approach to the discovery of selective mu-calpain inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.