benzyl 2-(9-(3-(5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido)benzyl)-3-chloro-9H-carbazol-7-yl)propanoate | 918547-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: benzyl 2-(9-(3-(5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido)benzyl)-3-chloro-9H-carbazol-7-yl)propanoate
• 英文别名: benzyl 2-[9-[[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]phenyl]methyl]-6-chlorocarbazol-2-yl]propanoate
• CAS: 918547-81-6
• 化学式: C₃₉H₃₉ClN₄O₄S
• 分子量: 695.282
• InChiKey: YYQJFULJHOVGKL-KGKTUKKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 2-(9-(3-(5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido)benzyl)-3-chloro-9H-carbazol-7-yl)propanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2-[9-[[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]phenyl]methyl]-6-chlorocarbazol-2-yl]propanoic acid
  参考文献：
  名称：

  Scaffold of the Cyclooxygenase-2 (COX-2) Inhibitor Carprofen Provides Alzheimer γ-Secretase Modulators

  摘要：

  N-Sulfonylated and N-alkylated carprofen derivatives were investigated for their inhibition and modulation of gamma-secretase, which is associated with Alzheimer's disease. The introduction of a lipophilic substituent transformed the COX-2 inhibitor carprofen into a potent gamma-secretase modulator. Several compounds (e.g., 9p, 11f) caused selective reduction of A beta(42) and an increase of A beta(38). The most active compounds displayed activities in the low micromolar range and no effect on the gamma-secretase cleavage at the epsilon-site.

  DOI：

  10.1021/jm0610200
• 作为产物：
  描述：

  卡洛芬 在 乙醇 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 生成 benzyl 2-(9-(3-(5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido)benzyl)-3-chloro-9H-carbazol-7-yl)propanoate
  参考文献：
  名称：

  Scaffold of the Cyclooxygenase-2 (COX-2) Inhibitor Carprofen Provides Alzheimer γ-Secretase Modulators

  摘要：

  N-Sulfonylated and N-alkylated carprofen derivatives were investigated for their inhibition and modulation of gamma-secretase, which is associated with Alzheimer's disease. The introduction of a lipophilic substituent transformed the COX-2 inhibitor carprofen into a potent gamma-secretase modulator. Several compounds (e.g., 9p, 11f) caused selective reduction of A beta(42) and an increase of A beta(38). The most active compounds displayed activities in the low micromolar range and no effect on the gamma-secretase cleavage at the epsilon-site.

  DOI：

  10.1021/jm0610200

文献信息

• Scaffold of the Cyclooxygenase-2 (COX-2) Inhibitor Carprofen Provides Alzheimer γ-Secretase Modulators
  作者：Rajeshwar Narlawar、Blanca I. Pérez Revuelta、Christian Haass、Harald Steiner、Boris Schmidt、Karlheinz Baumann

  DOI：10.1021/jm0610200

  日期：2006.12.1

  N-Sulfonylated and N-alkylated carprofen derivatives were investigated for their inhibition and modulation of gamma-secretase, which is associated with Alzheimer's disease. The introduction of a lipophilic substituent transformed the COX-2 inhibitor carprofen into a potent gamma-secretase modulator. Several compounds (e.g., 9p, 11f) caused selective reduction of A beta(42) and an increase of A beta(38). The most active compounds displayed activities in the low micromolar range and no effect on the gamma-secretase cleavage at the epsilon-site.