Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OCH3)-NH2 | 148528-99-8

• 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: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OCH3)-NH2
• 英文别名: Boc-Orn(Boc)(Boc)-Phe-Phe-Gly-Leu-Nva(OMe)(OMe)-NH2；tert-butyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-amino-5-methoxy-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-5-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopentan-2-yl]carbamate
• CAS: 148528-99-8
• 化学式: C₄₇H₇₂N₈O₁₁
• 分子量: 925.136
• InChiKey: BGESAYSQMVHZJY-LTLCPEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  66
• 可旋转键数：
  30
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  275
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OCH3)-NH2 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以72%的产率得到H-Orn-Phe-Phe-Gly-Leu-Nva(5-OCH3)-NH2
  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 、 盐酸 、 氨 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.03h， 生成 Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OCH3)-NH2
  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