5-[(2-甲基丙烷-2-基)氧基羰基氨基]-4-氧代-6-苯基-2-(苯基甲基)己酸 | 112070-31-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: 5-[(2-甲基丙烷-2-基)氧基羰基氨基]-4-氧代-6-苯基-2-(苯基甲基)己酸
• 英文名称: Boc-(RS)Pheψ(COCH2)(RS)Phe-OH
• 英文别名: 5-Amino-(N-t-butoxycarbonyl)-2-benzyl-4-oxo-6-phenylhexanoic acid；2-benzyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-6-phenylhexanoic acid
• CAS: 112070-31-2
• 化学式: C₂₄H₂₉NO₅
• 分子量: 411.498
• InChiKey: XPQONMQWEAQGDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(2-甲基丙烷-2-基)氧基羰基氨基]-4-氧代-6-苯基-2-(苯基甲基)己酸 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 H-(RS)Pheψ(COCH2)(RS)Phe-Gly-Leu-Met-NH2*HCl
  参考文献：
  名称：

  Dehydro ketomethylene and ketomethylene analogs of substance P: synthesis and biological activity

  摘要：

  The synthesis of dehydro keto methylene and keto methylene analogues of substance P using classical peptide synthesis is described. The following analogues were prepared: [pGlu6,Gly9psi(COCH2)(RS)Leu10]SP6-11 (4) and [pGlu6,-(RS)Phe7 psi(COCH2)(RS)Phe8]SP6-11 (8). The use of an improved deprotection scheme employing Meerwein's reagent (Et3OBF4) made possible the syntheses of the novel dehydro keto methylene analogue [pGlu6,(RS)Phe7 psi-(COCH2)delta(E)Phe8]SP6-11 (26) adn the tetrapeptide analogue [pGlu6,(RS)Phe8 psi(COCH2)Gly9]SP6-9(-OMe) (23). Compound 4 was a weak agonist in provoking contractions of the guinea pig ileum. Compound 26 was a potent inhibitor of SP degradation in rat hypothalamus preparations, with an IC50 value of 1.8 microM.

  DOI：

  10.1021/jm00397a026

文献信息

• EWENSON, ARIEL;LAUFER, RALPH;CHOREV, MICHAEL;SELINGER, ZVI;GILON, CHAIM, J. MED. CHEM., 31,(1988) N 2, 416-421
  作者：EWENSON, ARIEL、LAUFER, RALPH、CHOREV, MICHAEL、SELINGER, ZVI、GILON, CHAIM

  DOI：——

  日期：——
• Dehydro ketomethylene and ketomethylene analogs of substance P: synthesis and biological activity
  作者：Ariel Ewenson、Ralph Laufen、Michael Chorev、Zvi Selinger、Chaim Gilon

  DOI：10.1021/jm00397a026

  日期：1988.2

  The synthesis of dehydro keto methylene and keto methylene analogues of substance P using classical peptide synthesis is described. The following analogues were prepared: [pGlu6,Gly9psi(COCH2)(RS)Leu10]SP6-11 (4) and [pGlu6,-(RS)Phe7 psi(COCH2)(RS)Phe8]SP6-11 (8). The use of an improved deprotection scheme employing Meerwein's reagent (Et3OBF4) made possible the syntheses of the novel dehydro keto methylene analogue [pGlu6,(RS)Phe7 psi-(COCH2)delta(E)Phe8]SP6-11 (26) adn the tetrapeptide analogue [pGlu6,(RS)Phe8 psi(COCH2)Gly9]SP6-9(-OMe) (23). Compound 4 was a weak agonist in provoking contractions of the guinea pig ileum. Compound 26 was a potent inhibitor of SP degradation in rat hypothalamus preparations, with an IC50 value of 1.8 microM.