benzyl N-[(2S)-1-[2-[4-(1,3-dioxoisoindol-2-yl)butanoylamino]ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate | 135665-34-8

• 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: benzyl N-[(2S)-1-[2-[4-(1,3-dioxoisoindol-2-yl)butanoylamino]ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 135665-34-8
• 化学式: C₃₁H₃₂N₄O₆
• 分子量: 556.618
• InChiKey: ZALHGYUBYFOKDB-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133.91
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-1-[2-[4-(1,3-dioxoisoindol-2-yl)butanoylamino]ethylamino]-1-oxo-3-phenylpropan-2-yl]carbamate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.32 kPa 条件下， 生成 1-(phenylalanyl)-4-(4-phthalimidobutyryl)-1,4-diazabutane
  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：

  4-(1,3-二氧代异吲哚啉-2-基)丁酰氯 、 [(S)-1-(2-Amino-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester; hydrochloride 在 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到benzyl N-[(2S)-1-[2-[4-(1,3-dioxoisoindol-2-yl)butanoylamino]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