(S)-2-[(S)-5-Benzyloxycarbonylamino-1-((S)-2-dodecylcarbamoyl-pyrrolidine-1-carbonyl)-pentylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester | 148417-54-3

• 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: (S)-2-[(S)-5-Benzyloxycarbonylamino-1-((S)-2-dodecylcarbamoyl-pyrrolidine-1-carbonyl)-pentylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-2-[[(2S)-1-[(2S)-2-(dodecylcarbamoyl)pyrrolidin-1-yl]-1-oxo-6-(phenylmethoxycarbonylamino)hexan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 148417-54-3
• 化学式: C₄₁H₆₇N₅O₇
• 分子量: 742.012
• InChiKey: POYKQORKBJALCE-IMKBVMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  53
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-5-Benzyloxycarbonylamino-1-((S)-2-dodecylcarbamoyl-pyrrolidine-1-carbonyl)-pentylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 生成 {(S)-6-((S)-2-Dodecylcarbamoyl-pyrrolidin-1-yl)-6-oxo-5-[((S)-pyrrolidine-2-carbonyl)-amino]-hexyl}-carbamic acid benzyl ester; compound with trifluoro-acetic acid
  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：

  BOC-L-脯氨酸 在 N-甲基吗啉 作用下， 反应 0.08h， 生成 (S)-2-[(S)-5-Benzyloxycarbonylamino-1-((S)-2-dodecylcarbamoyl-pyrrolidine-1-carbonyl)-pentylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
  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