4-cyclohexyl-1-(3-amino-4-methylphenyl)butan-1-one | 180136-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-cyclohexyl-1-(3-amino-4-methylphenyl)butan-1-one
• 英文别名: 1-(3-Amino-4-methylphenyl)-4-cyclohexylbutan-1-one
• CAS: 180136-27-0
• 化学式: C₁₇H₂₅NO
• 分子量: 259.392
• InChiKey: BPHMPCKIZKQOIX-UHFFFAOYSA-N

物化性质

• 沸点：
  429.3±25.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-cyclohexyl-1-(3-amino-4-methylphenyl)butan-1-one 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 N-[5-(4-cyclohexylbutyryl)-2-methylphenyl]-4-hydroxybenzamide
  参考文献：
  名称：

  New Low-Density Lipoprotein Receptor Upregulators Acting via a Novel Mechanism

  摘要：

  The synthesis and biological activity of a new series of benzamides and related compounds that upregulate the expression of the low-density lipoprotein (LDL) receptor in human hepatocytes (HepG2 cells) by a novel mechanism are described. The lead compound, N-[5-[(3-cyclohexylpropionyl)amino]-2-methylphenyl]-4-hydroxybenzamide (1, RPR102359), increased the expression of the LDL receptors in HepG2 cells by 80% when tested at a concentration of 3 mu M. Mevinolin (lovastatin) was found to increase the LDL receptor expression by 70% at the same concentration. In contrast to mevinolin, 1 was found to have no effect on cholesterol biosynthesis in liver homogenates or in HepG2 cells at doses where substantial upregulation of the LDL receptor was observed and thus stimulated LDL receptor expression by a novel mechanism.

  DOI：

  10.1021/jm960153q
• 作为产物：
  描述：

  4-环己基丁酰氯 在 palladium on activated charcoal 三氯化铝 、 硫酸 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， -7.0~25.0 ℃ 、101.33 kPa 条件下， 反应 17.83h， 生成 4-cyclohexyl-1-(3-amino-4-methylphenyl)butan-1-one
  参考文献：
  名称：

  New Low-Density Lipoprotein Receptor Upregulators Acting via a Novel Mechanism

  摘要：

  The synthesis and biological activity of a new series of benzamides and related compounds that upregulate the expression of the low-density lipoprotein (LDL) receptor in human hepatocytes (HepG2 cells) by a novel mechanism are described. The lead compound, N-[5-[(3-cyclohexylpropionyl)amino]-2-methylphenyl]-4-hydroxybenzamide (1, RPR102359), increased the expression of the LDL receptors in HepG2 cells by 80% when tested at a concentration of 3 mu M. Mevinolin (lovastatin) was found to increase the LDL receptor expression by 70% at the same concentration. In contrast to mevinolin, 1 was found to have no effect on cholesterol biosynthesis in liver homogenates or in HepG2 cells at doses where substantial upregulation of the LDL receptor was observed and thus stimulated LDL receptor expression by a novel mechanism.

  DOI：

  10.1021/jm960153q