N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-nitrobenzamide | 180136-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-nitrobenzamide
• 英文别名: N-[5-(3-cyclohexylpropanoylamino)-2-methylphenyl]-4-nitrobenzamide
• CAS: 180136-39-4
• 化学式: C₂₃H₂₇N₃O₄
• 分子量: 409.485
• InChiKey: SJJLVULJYAJYEA-UHFFFAOYSA-N

物化性质

• 沸点：
  561.9±50.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-nitrobenzamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以63%的产率得到N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-aminobenzamide
  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：

  3-环己基丙酰氯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-nitrobenzamide
  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

• RAF KINASE INHIBITORS
  申请人：ZENECA LIMITED

  公开号：EP0941084A1

  公开（公告）日：1999-09-15
• AMIDE DERIVATIVES FOR THE TREATMENT OF DISEASES MEDIATED BY CYTOKINES
  申请人：AstraZeneca UK Limited

  公开号：EP1017378A1

  公开（公告）日：2000-07-12
• JP2001517620A
  申请人：——

  公开号：JP2001517620A

  公开（公告）日：2001-10-09
• Amide derivatives for the treatment of diseases mediated by cytokines
  申请人：ZENECA LIMITED

  公开号：US20030166730A1

  公开（公告）日：2003-09-04

  The invention concerns the use of amide derivatives of formula (I) wherein: R 1 and R 2 are substituents such as hydroxy, C 1-6 alkoxy, mercapto, C 1-6 alkylthio, amino, C 1-6 alkylamino and di-(C 1-6 alkyl)amino; m and p are independently 0-3; R 3 is C 1-4 alkyl; q is 0-4; and R 4 is aryl or cycloalkyl; or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for use in the treatment of diseases or medical conditions mediated by cytokines.
• US6498274B1
  申请人：——

  公开号：US6498274B1

  公开（公告）日：2002-12-24