-SP-OMe | 101835-76-1

• 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: -SP-OMe
• 英文别名: α-Z-Arg¹,D-Pro²,N^ε-Z-Lys³,Asn⁵,Arg⁶,D-Phe^7,8,Gly⁹ψ(CH2S)-D-Leu¹⁰,D-Met¹¹>-SP-OMe
• CAS: 101835-76-1
• 化学式: C₈₀H₁₁₄N₁₈O₁₆S₂
• 分子量: 1648.03
• InChiKey: FHRBUNBIXKSJSJ-YCFDEZORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  116.0
• 可旋转键数：
  49.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  514.17
• 氢给体数：
  16.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  BOC-L-天冬酰胺 、 Boc-D-苯丙氨酸 、 N-Boc-D-蛋氨酸 、 Boc-Glyψ(CH2S)-D-Leu-OH 、 alkaline earth salt of/the/ methylsulfuric acid 生成 -SP-OMe
  参考文献：
  名称：

  Antagonists of substance P. Further modifications of SP antagonists obtained by replacing either positions 7, 9 or 7, 8 and 11 of SP with D-amino acid residues

  摘要：

  Antagonists of SP and the C-terminal (6-11)-hexapeptide have been obtained by multiple D-amino acid substitutions in various positions of SP and by protecting the N alpha-Arg1 and N epsilon Lys3 amino groups with benzyloxycarbonyl groups. On the guinea pig ileum a number of these antagonized both SP and the hexapeptide. Except [N alpha-Z-Arg1,D-Pro2,N epsilon-Z-Lys3,Asn5,Arg6,D-Phe7,D-Trp9]-SP-OMe (4) and the corresponding amide 7, which were more potent antagonists of SP than the hexapeptide, all the others, e.g., [N alpha-Z-Arg1,D-Pro2,4,N epsilon-Z-Lys3,D-Phe7,8,Sar9,D-Met11]-SP-OMe (9), [N alpha-Z-Arg1,D-Pro2,4,N epsilon-Z-Lys3,D-Phe7,8,Sar9,MeLeu10,D-Met11]-SP -OMe (11), were more potent antagonists of the hexapeptide. On the rat spinal cord preparation, most of the antagonists were only active against the hexapeptide. A few antagonized SP, but these also reduced carbachol or both carbachol and glutamate responses. Two of the antagonists, [D-Pro2,Asn5,Lys6,D-Phe7,D-Trp9]-SP-OMe (2) and [Boc-D-Pro4,D-Phe7,8,Sar9,D-Met11]-SP(4-11)-OMe (10), were inactive on the ileum but still antagonized the hexapeptide on the spinal cord. The smallest peptides to antagonize SP and the hexapeptide were two heptapeptides, 6 and 21, [Z-Asn5,Arg6,D-Phe7,8,Gly9 psi (CH2S)D-Leu10,D-Met11]-SP(5-11)-OMe (21) being more potent than 6. None of the antagonists showed significant analgesic activity without side effects. Some of the antagonists were shown to release histamine from isolated rat peritoneal cells.

  DOI：

  10.1021/jm00157a009