7-(cyclohexylamino)-7-oxoheptanoic acid | 93189-53-8

• 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: 7-(cyclohexylamino)-7-oxoheptanoic acid
• 英文别名: Pimelinsaeure-mono-cyclohexylamid；Pimelinsaeure-cyclohexylamid；N-cyclohexylpimelamic acid
• CAS: 93189-53-8
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: ANDBTFQTMIPLCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 7-(cyclohexylamino)-7-oxoheptanoic acid 生成 Pimelinsaeure-methylester-cyclohexylamid
  参考文献：
  名称：

  ?-Dicarbonyl compounds Communication 20. Reaction of 2-(alkylaminomethylene) cyclohexanones with hydrogen peroxide

  摘要：

  DOI：

  10.1007/bf01141651
• 作为产物：
  描述：

  庚二酸 在 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 7-(cyclohexylamino)-7-oxoheptanoic acid
  参考文献：
  名称：

  A Potent Isoprenylcysteine Carboxylmethyltransferase (ICMT) Inhibitor Improves Survival in Ras-Driven Acute Myeloid Leukemia

  摘要：

  Blockade of Ras activity by inhibiting its post-translational methylation catalyzed by isoprenylcysteine carboxylmethyltransferase (ICMT) has been suggested as a promising antitumor strategy. However, the paucity of inhibitors has precluded the clinical validation of this approach. In this work we report a potent ICMT inhibitor, compound 3 [UCM-1336, IC50 = 2 mu M], which is selective against the other enzymes involved in the post-translational modifications of Ras. Compound 3 significantly impairs the membrane association of the four Ras isoforms, leading to a decrease of Ras activity and to inhibition of Ras downstream signaling pathways. In addition, it induces cell death in a variety of Ras-mutated tumor cell lines and increases survival in an in vivo model of acute myeloid leukemia. Because ICMT inhibition impairs the activity of the four Ras isoforms regardless of its activating mutation, compound 3 surmounts many of the common limitations of available Ras inhibitors described so far. In addition, these results validate ICMT as a valuable target for the treatment of Ras-driven tumors.

  DOI：

  10.1021/acs.jmedchem.9b00145