benzyl N-[(2S)-1-[2-(2-hydroxyethylamino)ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate | 789458-38-4

• 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: benzyl N-[(2S)-1-[2-(2-hydroxyethylamino)ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 789458-38-4
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: WSAPZXOGTFKIFD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.69
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-[2-(2-hydroxyethylamino)ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl N-[(2S)-1-[2-[4-(1,3-dioxoisoindol-2-yl)butanoyl-[2-[4-(1,3-dioxoisoindol-2-yl)butanoyl-[2-[4-(1,3-dioxoisoindol-2-yl)butanoylamino]ethyl]amino]ethyl]amino]ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Modification of the enkephalin "message" with an artificial polycationic C-terminus

  摘要：

  The C-terminal ''address'' sequences of prodynorphin-drived opioid peptides contain an unusually high proportion of basic residues, which are known to be crucial for conferring high activity and selectivity for kappa-opioid receptors. In an effort to investigate the possibility that the polycationic ''tails'' may be involved in a coulombic interaction with a complementary polyanionic receptor domain, we attached a series of achiral peptide-like cationic fragments to the C-terminus of the opioid peptide ''message'', Tyr-Gly-Gly-Phe. Binding of the various compounds to opioid receptor types in guinea pig brain membranes was weak, and the pharmacologic activities in the guinea pig ileum were marginal. These results indicate either that the chosen ligand design does not satisfy the structural requirements of the hypothesized coulombic interaction or that the latter is a minor criterion governing receptor recognition.

  DOI：

  10.1021/jm00113a020
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 、 羟乙基乙二胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到benzyl N-[(2S)-1-[2-(2-hydroxyethylamino)ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Modification of the enkephalin "message" with an artificial polycationic C-terminus

  摘要：

  The C-terminal ''address'' sequences of prodynorphin-drived opioid peptides contain an unusually high proportion of basic residues, which are known to be crucial for conferring high activity and selectivity for kappa-opioid receptors. In an effort to investigate the possibility that the polycationic ''tails'' may be involved in a coulombic interaction with a complementary polyanionic receptor domain, we attached a series of achiral peptide-like cationic fragments to the C-terminus of the opioid peptide ''message'', Tyr-Gly-Gly-Phe. Binding of the various compounds to opioid receptor types in guinea pig brain membranes was weak, and the pharmacologic activities in the guinea pig ileum were marginal. These results indicate either that the chosen ligand design does not satisfy the structural requirements of the hypothesized coulombic interaction or that the latter is a minor criterion governing receptor recognition.

  DOI：

  10.1021/jm00113a020