8-(3-methoxy-3-oxopropylamino)-8-oxooctanoic acid | 1251828-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-(3-methoxy-3-oxopropylamino)-8-oxooctanoic acid
• 英文别名: 8-[(3-Methoxy-3-oxopropyl)amino]-8-oxooctanoic acid；8-[(3-methoxy-3-oxopropyl)amino]-8-oxooctanoic acid
• CAS: 1251828-46-2
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: GBFQRRVWUFHLOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-甲基-2-丙基[(甲硫基)亚氨代甲酰基]氨基甲酸酯 、 8-(3-methoxy-3-oxopropylamino)-8-oxooctanoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到methyl 3-{8-[boc-amino(methylthio)methyleneamino]-8-oxooctanamido}propanoate
  参考文献：
  名称：

  NG-Acyl-argininamides as NPY Y1 receptor antagonists: Influence of structurally diverse acyl substituents on stability and affinity

  摘要：

  N-G-Acylated argininamides, covering a broad range of lipophilicity (calculated log D values: -1.8-12.5), were synthesized and investigated for NPY Y-1 receptor (Y1R) antagonism, Y1R affinity and stability in buffer (N-G-deacylation, yielding BIBP 3226). Broad structural variation of substituents was tolerated. The K-i (binding) and K-b values (Y1R antagonism) varied from low nM to one-digit mu M. Most of the compounds proved to be sufficiently stable at pH 7.4 over 90 min to determine reliable pharmacological data in vitro. Exceptionally high instability was detected when a succinyl moiety was attached to the guanidine, probably, due to an intramolecular cleavage mechanism. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.028
• 作为产物：
  描述：

  benzyl 8-(3-methoxy-3-oxopropylamino)-8-oxooctanoate 在 palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、1.2 MPa 条件下， 以94%的产率得到8-(3-methoxy-3-oxopropylamino)-8-oxooctanoic acid
  参考文献：
  名称：

  NG-Acyl-argininamides as NPY Y1 receptor antagonists: Influence of structurally diverse acyl substituents on stability and affinity

  摘要：

  N-G-Acylated argininamides, covering a broad range of lipophilicity (calculated log D values: -1.8-12.5), were synthesized and investigated for NPY Y-1 receptor (Y1R) antagonism, Y1R affinity and stability in buffer (N-G-deacylation, yielding BIBP 3226). Broad structural variation of substituents was tolerated. The K-i (binding) and K-b values (Y1R antagonism) varied from low nM to one-digit mu M. Most of the compounds proved to be sufficiently stable at pH 7.4 over 90 min to determine reliable pharmacological data in vitro. Exceptionally high instability was detected when a succinyl moiety was attached to the guanidine, probably, due to an intramolecular cleavage mechanism. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.028

文献信息

• NG-Acyl-argininamides as NPY Y1 receptor antagonists: Influence of structurally diverse acyl substituents on stability and affinity
  作者：Stefan Weiss、Max Keller、Günther Bernhardt、Armin Buschauer、Burkhard König

  DOI：10.1016/j.bmc.2010.07.028

  日期：2010.9

  N-G-Acylated argininamides, covering a broad range of lipophilicity (calculated log D values: -1.8-12.5), were synthesized and investigated for NPY Y-1 receptor (Y1R) antagonism, Y1R affinity and stability in buffer (N-G-deacylation, yielding BIBP 3226). Broad structural variation of substituents was tolerated. The K-i (binding) and K-b values (Y1R antagonism) varied from low nM to one-digit mu M. Most of the compounds proved to be sufficiently stable at pH 7.4 over 90 min to determine reliable pharmacological data in vitro. Exceptionally high instability was detected when a succinyl moiety was attached to the guanidine, probably, due to an intramolecular cleavage mechanism. (C) 2010 Elsevier Ltd. All rights reserved.