N-dodecyl-t-BOC-(S)-prolineamide | 110139-27-0

• 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: N-dodecyl-t-BOC-(S)-prolineamide
• 英文别名: tert-butyl (2S)-2-(dodecylcarbamoyl)pyrrolidine-1-carboxylate
• CAS: 110139-27-0
• 化学式: C₂₂H₄₂N₂O₃
• 分子量: 382.587
• InChiKey: NFPNSXZISIQROZ-IBGZPJMESA-N

物化性质

• 沸点：
  516.1±39.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-dodecyl-t-BOC-(S)-prolineamide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以98%的产率得到H-Pro-NHC12H25-n*HCl
  参考文献：
  名称：

  JP2005/41863

  摘要：

  公开号：
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 N-甲基吗啉 作用下， 反应 0.08h， 生成 N-dodecyl-t-BOC-(S)-prolineamide
  参考文献：
  名称：

  Synthesis of new substance P analogues releasing histamine from rat peritoneal mast cells

  摘要：

  New analogues of the N-terminal fragment of substance P [Arg-Pro-Lys-Pro, SP(1-4)] were synthesized and their activities on histamine release from rat peritoneal mast cells were compared. The potency of these compounds decreases in the following order (in abbreviation): SP(1-4)-C-12 > C-12''-SP(1-4)-OCH3 > C-12''-SP(1-4)-OH, H-Lys-Pro-C-12 and SP. Benzalkonium chloride, a competitive antagonist of peptide-induced histamine release from rat mast cells, inhibits the effect of SP and SP analogues with IC50 in the range of micromolar concentrations. SP(1-4)-C-12 and C-12''-SP(1-4)-OCH, have been found to be 10-fold more active than SP on the GTPase activity of purified G proteins (G(o)/G(i)). The lack of clear structural relationships for agonist activities supports a receptor-less mechanism for histamine release by SP and its analogs. This effect could be elicited by a direct stimulation of G proteins.

  DOI：

  10.1016/0223-5234(92)90025-v

文献信息

• JP2005/41863
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of new substance P analogues releasing histamine from rat peritoneal mast cells
  作者：Y Chen、M Mousli、S Thoret、T Fischer、Y Landry、R Michelot

  DOI：10.1016/0223-5234(92)90025-v

  日期：1992.12

  New analogues of the N-terminal fragment of substance P [Arg-Pro-Lys-Pro, SP(1-4)] were synthesized and their activities on histamine release from rat peritoneal mast cells were compared. The potency of these compounds decreases in the following order (in abbreviation): SP(1-4)-C-12 > C-12''-SP(1-4)-OCH3 > C-12''-SP(1-4)-OH, H-Lys-Pro-C-12 and SP. Benzalkonium chloride, a competitive antagonist of peptide-induced histamine release from rat mast cells, inhibits the effect of SP and SP analogues with IC50 in the range of micromolar concentrations. SP(1-4)-C-12 and C-12''-SP(1-4)-OCH, have been found to be 10-fold more active than SP on the GTPase activity of purified G proteins (G(o)/G(i)). The lack of clear structural relationships for agonist activities supports a receptor-less mechanism for histamine release by SP and its analogs. This effect could be elicited by a direct stimulation of G proteins.