N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-methoxycarbonylbenzamide | 180136-36-1

• 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-methoxycarbonylbenzamide
• 英文别名: Methyl 4-[[5-(3-cyclohexylpropanoylamino)-2-methylphenyl]carbamoyl]benzoate
• CAS: 180136-36-1
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: VVMCJOXDFDNJSM-UHFFFAOYSA-N

物化性质

• 沸点：
  558.2±50.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.5
• 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-methoxycarbonylbenzamide 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以63%的产率得到N-[5-(3-cyclohexylpropionamido)-2-methylphenyl]-4-hydroxymethylbenzamide
  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-methoxycarbonylbenzamide
  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

• Amide derivatives for the treatment of diseases mediated by cytokines
  申请人：Zeneca Limited

  公开号：US06498274B1

  公开（公告）日：2002-12-24

  The invention concerns the use of amide derivatives of formula (I) wherein: R1 and R2 are substituents such as hydroxy, C1-6alkoxy, mercapto, C1-6alkylthio, amino, C1-6alkylamino and di-(C1-6alkyl)amino; m and p are independently 0-3R3 is C1-4alkyl; q is 0-4; and R4 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

  该发明涉及使用式(I)的酰胺衍生物，其中：R1和R2是取代基，如羟基、C1-6烷氧基、巯基、C1-6烷基硫基、氨基、C1-6烷基氨基和二-(C1-6烷基)氨基；m和p独立地为0-3；R3为C1-4烷基；q为0-4；R4为芳基或环烷基；或其在制备用于治疗由细胞因子介导的疾病或医疗状况的药物中的药用盐。
• 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
• US6498274B1
  申请人：——

  公开号：US6498274B1

  公开（公告）日：2002-12-24