(S)-5-Methoxy-2-[(S)-2-(4-methoxy-benzyloxycarbonylamino)-4-methyl-pentanoylamino]-pentanoic acid methyl ester | 148528-94-3

• 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)-5-Methoxy-2-[(S)-2-(4-methoxy-benzyloxycarbonylamino)-4-methyl-pentanoylamino]-pentanoic acid methyl ester
• 英文别名: methyl (2S)-5-methoxy-2-[[(2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-4-methylpentanoyl]amino]pentanoate
• CAS: 148528-94-3
• 化学式: C₂₂H₃₄N₂O₇
• 分子量: 438.521
• InChiKey: USIBRDRSXILDCL-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-5-Methoxy-2-[(S)-2-(4-methoxy-benzyloxycarbonylamino)-4-methyl-pentanoylamino]-pentanoic acid methyl ester 在 盐酸 、 氨 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (S)-2-Amino-4-methyl-pentanoic acid ((S)-1-carbamoyl-4-methoxy-butyl)-amide; hydrochloride
  参考文献：
  名称：

  Synthesis of an analogue of the substance P C-terminal hexapeptide with modification at the glutaminyl and methioninyl residues and increased activity in NK-2 receptor type: Structure-activity relationships

  摘要：

  Analogues of [Orn6]-Sp6-11 have been synthesized in which the Met11 residue is replaced by Hse(CH3), Hse(Bzl), Nva(5-OCH3), Nva(5-OBzl) and Abu. These analogues were tested in 3 in vitro preparations representative of NK-1, NK-2 and NK-3 receptor types. The Hse(Bzl) analogue is 16.6-fold more potent than the parent hexapeptide at the NK-2 receptor and 2.4-fold more potent at the NK-3 receptor. The Nva(5-OCH3) analogues howed weak antagonist activity in NK-2 and NK-3 receptor types, being a full agonist at NK-1. It is concluded from structure-activity correlations that the role of Met11 side chain in substance P is associated with activity and/or efficacy, as appropriate modifications in the side chain may result either in agonists with increased activity compared to the parent hexapeptide or selective agonists or may induce antagonism.

  DOI：

  10.1016/0223-5234(92)90027-x
• 作为产物：
  描述：

  (2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-4-甲基戊酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.03h， 生成 (S)-5-Methoxy-2-[(S)-2-(4-methoxy-benzyloxycarbonylamino)-4-methyl-pentanoylamino]-pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of an analogue of the substance P C-terminal hexapeptide with modification at the glutaminyl and methioninyl residues and increased activity in NK-2 receptor type: Structure-activity relationships

  摘要：

  Analogues of [Orn6]-Sp6-11 have been synthesized in which the Met11 residue is replaced by Hse(CH3), Hse(Bzl), Nva(5-OCH3), Nva(5-OBzl) and Abu. These analogues were tested in 3 in vitro preparations representative of NK-1, NK-2 and NK-3 receptor types. The Hse(Bzl) analogue is 16.6-fold more potent than the parent hexapeptide at the NK-2 receptor and 2.4-fold more potent at the NK-3 receptor. The Nva(5-OCH3) analogues howed weak antagonist activity in NK-2 and NK-3 receptor types, being a full agonist at NK-1. It is concluded from structure-activity correlations that the role of Met11 side chain in substance P is associated with activity and/or efficacy, as appropriate modifications in the side chain may result either in agonists with increased activity compared to the parent hexapeptide or selective agonists or may induce antagonism.

  DOI：

  10.1016/0223-5234(92)90027-x