N-{3-[2-cyano-2-(4-hydroxyphenyl)vinyl]-4-methylphenyl}-3-cyclohexylpropionamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: N-{3-[2-cyano-2-(4-hydroxyphenyl)vinyl]-4-methylphenyl}-3-cyclohexylpropionamide
• 英文别名: N-[3-[(Z)-2-cyano-2-(4-hydroxyphenyl)ethenyl]-4-methylphenyl]-3-cyclohexylpropanamide
• 化学式: C₂₅H₂₈N₂O₂
• 分子量: 388.51
• InChiKey: XSJQTFSLXWFHHQ-PXLXIMEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2-甲基-5-硝基-苯基)-甲醇 在 palladium on activated charcoal manganese(IV) oxide 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 49.0h， 生成 N-{3-[2-cyano-2-(4-hydroxyphenyl)vinyl]-4-methylphenyl}-3-cyclohexylpropionamide
  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

文献信息

• New Low-Density Lipoprotein Receptor Upregulators Acting <i>via</i> a Novel Mechanism
  作者：Michael J. Ashton、Thomas J. Brown、Garry Fenton、Frank Halley、Mark F. Harper、Peter M. Lockey、Barry Porter、Alan G. Roach、Keith A. J. Stuttle、Nigel Vicker、Roger J. A. Walsh

  DOI：10.1021/jm960153q

  日期：1996.1.1

  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.