1H-Imidazole-1-carboxylic acid, (2R)-2-methoxy-3-(octadecyloxy)propylester | 498555-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1H-Imidazole-1-carboxylic acid, (2R)-2-methoxy-3-(octadecyloxy)propylester
• 英文别名: Imidazole-1-carboxylic acid (R)-2-methoxy-3-octadecyloxy-propyl ester
• CAS: 498555-00-3
• 化学式: C₂₆H₄₈N₂O₄
• 分子量: 452.678
• InChiKey: YLBKOZVQVCMUAR-RUZDIDTESA-N

物化性质

• 沸点：
  547.1±60.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  32.0
• 可旋转键数：
  22.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  62.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1H-Imidazole-1-carboxylic acid, (2R)-2-methoxy-3-(octadecyloxy)propylester 在 20percent Pd(OH)2/C 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 SH-8
  参考文献：
  名称：

  Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt

  摘要：

  The synthesis from l-quebrachitol of a series of 3-deoxygenated ether lipid-type phosphatidylinositol (PI) analogues is reported, that selectively block activation of Akt and downstream substrates without affecting activation of the upstream kinase, PDK-1, or other kinases downstream of ras such as MAPK in H157 and H1703 lung cancer cells that have high levels of constitutively active Akt. The 2-hydroxyl in these compounds was deleted or alkylated with the intent to preclude metabolic degradation of these compounds by PI-specific phospholipase C (PI-PLC). PI analogues with phosphate linkers are more effective than those with carbonate linkers. Specific inhibition of Akt by these compounds validates ligand design targeted to the PH domains of crucial signaling proteins, thus providing a unique class of possible cancer therapeutics.

  DOI：

  10.1021/ja0285159
• 作为产物：
  描述：

  (2S)-2-甲氧基-3-(十八烷氧基)-1-丙醇 、 N,N'-羰基二咪唑 以 甲苯 为溶剂， 反应 2.0h， 生成 1H-Imidazole-1-carboxylic acid, (2R)-2-methoxy-3-(octadecyloxy)propylester
  参考文献：
  名称：

  Novel PI Analogues Selectively Block Activation of the Pro-survival Serine/Threonine Kinase Akt

  摘要：

  The synthesis from l-quebrachitol of a series of 3-deoxygenated ether lipid-type phosphatidylinositol (PI) analogues is reported, that selectively block activation of Akt and downstream substrates without affecting activation of the upstream kinase, PDK-1, or other kinases downstream of ras such as MAPK in H157 and H1703 lung cancer cells that have high levels of constitutively active Akt. The 2-hydroxyl in these compounds was deleted or alkylated with the intent to preclude metabolic degradation of these compounds by PI-specific phospholipase C (PI-PLC). PI analogues with phosphate linkers are more effective than those with carbonate linkers. Specific inhibition of Akt by these compounds validates ligand design targeted to the PH domains of crucial signaling proteins, thus providing a unique class of possible cancer therapeutics.

  DOI：

  10.1021/ja0285159