tert-butyl N-[6-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-6-oxohexyl]carbamate | 148417-52-1

• 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: tert-butyl N-[6-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-6-oxohexyl]carbamate
• CAS: 148417-52-1
• 化学式: C₂₈H₅₃N₃O₄
• 分子量: 495.747
• InChiKey: YZWQCJXJICYIIG-DEOSSOPVSA-N

物化性质

• 沸点：
  669.7±55.0 °C(predicted)
• 密度：
  1.004±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[6-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-6-oxohexyl]carbamate 在 silver(I) chloride 、 calcium oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [6-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-6-oxohexyl]-trimethylazanium;chloride
  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
• 作为产物：
  描述：

  叔丁氧羰酰基6-氨基己酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 tert-butyl N-[6-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-6-oxohexyl]carbamate
  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

• 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.