苯酰胺,4-(乙酰氧基)-N-(2-甲基-5-硝基苯基)- | 180136-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯酰胺,4-(乙酰氧基)-N-(2-甲基-5-硝基苯基)-
• 英文名称: 4-acetoxy-N-(2-methyl-5-nitrophenyl)benzamide
• 英文别名: N-(2-methyl-5-nitrophenyl)-4-acetoxybenzamide；4-[(2-Methyl-5-nitrophenyl)carbamoyl]phenyl acetate；[4-[(2-methyl-5-nitrophenyl)carbamoyl]phenyl] acetate
• CAS: 180136-44-1
• 化学式: C₁₆H₁₄N₂O₅
• mdl: MFCD00834080
• 分子量: 314.298
• InChiKey: JODYLBSAUUOWOK-UHFFFAOYSA-N

物化性质

• 沸点：
  407.5±45.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯酰胺,4-(乙酰氧基)-N-(2-甲基-5-硝基苯基)- 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 43.0h， 生成 N-[5-(3-cyclopentylpropionamido)-2-methylphenyl]-4-acetoxybenzamide
  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-acetoxybenzoyl chloride 、 2-氨基-4-硝基甲苯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以33%的产率得到苯酰胺,4-(乙酰氧基)-N-(2-甲基-5-硝基苯基)-
  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

• Bezamide derivatives for the treatment of diseases mediated by cytokines
  申请人：AstraZeneca AB

  公开号：US06579872B1

  公开（公告）日：2003-06-17

  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 0-3; R3 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.

  本发明涉及使用式（I）的酰胺衍生物，其中：R1和R2是取代基，例如羟基，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；而R4为芳基或环烷基；或其药学上可接受的盐制剂，用于制造治疗因细胞因子介导的疾病或医疗条件的药物。
• 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。
• Benzamide derivatives for the treatment of diseases mediated by cytokines
  申请人：ASTRAZENECA AB

  公开号：US20030212068A1

  公开（公告）日：2003-11-13

  1 The invention concerns amide derivatives of Formula (I), wherein R 3 is (1-6C)alkyl or halogeno; m is 1-3 and R 1 is selected from substituents such as: (A) hydroxy, halogeno, (1-6C)alkyl, (1-6C)alkoxy, aryl, heteroaryl and heterocyclyl; and (B) di-[(1-6C)alkyl]amino-(1-6C)alkyl, (1-6C)alkoxy-(2-6C)alkoxy, di-[(1-6C)alkyl]amino-(2-6C)alkoxy, aryloxy, heteroaryloxy, heteroaryl-(1-6C)alkoxy, heterocyclyloxy and heterocyclyl-(1-6C)alkoxy; p is 0-2 and R 2 is a substituent such as hydroxy and halogeno; q is 0-4; and R 4 is aryl or cycloalkyl which bears 1-3 substituents such as: (C) hydrogen, hydroxy, halogeno and heterocyclyl; and (D) heteroaryl-(1-6C)alkoxy and heterocyclyl-(1-6C)alkoxy, provided that a substituent on R 4 is selected from paragraph (C) only if at least one R 1 group is selected from paragraph (B); processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.

  该发明涉及式(I)的酰胺衍生物，其中R3是(1-6C)烷基或卤素；m为1-3，R1被选择为以下取代基之一：(A)羟基、卤素、(1-6C)烷基、(1-6C)烷氧基、芳基、杂芳基和杂环基；和(B)二-[(1-6C)烷基]氨基-(1-6C)烷基、(1-6C)烷氧基-(2-6C)烷氧基、二-[(1-6C)烷基]氨基-(2-6C)烷氧基、芳氧基、杂芳氧基、杂芳基-(1-6C)烷氧基、杂环氧基和杂环基-(1-6C)烷氧基；p为0-2，R2是羟基和卤素等取代基；q为0-4；R4是芳基或环烷基，其带有1-3个取代基，例如：(C)氢、羟基、卤素和杂环基；和(D)杂芳基-(1-6C)烷氧基和杂环基-(1-6C)烷氧基，但仅当至少一个R1基团选择自段(B)时，才从段(C)中选择R4上的取代基；制备它们的方法，含有它们的制药组合物，以及它们在治疗由细胞因子介导的疾病或医疗状况中的应用。
• 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