Butyl 3-nitro-5-(trifluoromethyl)benzoate | 203513-23-9

• 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: Butyl 3-nitro-5-(trifluoromethyl)benzoate
• CAS: 203513-23-9
• 化学式: C₁₂H₁₂F₃NO₄
• 分子量: 291.227
• InChiKey: XAOBCPQUHMZELJ-UHFFFAOYSA-N

物化性质

• 沸点：
  330.3±42.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Butyl 3-nitro-5-(trifluoromethyl)benzoate 在 palladium on activated charcoal Amberlyst A-21 ion-exchange resin 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 18.3h， 生成 3-[(2-Chloro-4-trifluoromethyl-pyrimidine-5-carbonyl)-amino]-5-trifluoromethyl-benzoic acid butyl ester
  参考文献：
  名称：

  2-Chloro-4-(trifluoromethyl)pyrimidine-5-N-(3‘,5‘-bis(trifluoromethyl)phenyl)- carboxamide:  A Potent Inhibitor of NF-κB- and AP-1-Mediated Gene Expression Identified Using Solution-Phase Combinatorial Chemistry

  摘要：

  Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-kB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution-phase parallel synthesis, inhibitors of both NF-kB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-kB as potential therapeutic targets. The synthesis and preliminary structure-activity relationships of these compounds is addressed.

  DOI：

  10.1021/jm970671g
• 作为产物：
  描述：

  3-硝基-5-(三氟甲基)苯甲酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 Butyl 3-nitro-5-(trifluoromethyl)benzoate
  参考文献：
  名称：

  2-Chloro-4-(trifluoromethyl)pyrimidine-5-N-(3‘,5‘-bis(trifluoromethyl)phenyl)- carboxamide:  A Potent Inhibitor of NF-κB- and AP-1-Mediated Gene Expression Identified Using Solution-Phase Combinatorial Chemistry

  摘要：

  Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-kB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution-phase parallel synthesis, inhibitors of both NF-kB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-kB as potential therapeutic targets. The synthesis and preliminary structure-activity relationships of these compounds is addressed.

  DOI：

  10.1021/jm970671g

文献信息

• BENZOIC ACID DERIVATIVES, METHODS AND USES THEREOF
  申请人：Faculdade de Farmácia da Universidade de Lisboa

  公开号：EP4345091A1

  公开（公告）日：2024-04-03

  The present disclosure relates to novel benzoic acid derivatives, specifically esters and benzamides, and their obtention. Furthermore, the present disclosure relates to the use of such compounds in medicine or veterinary, specifically, in the prevention or treatment of tuberculosis.

  本公开涉及一种新型苯甲酸衍生物，特别是酯和苯甲酰胺及其制备方法。而且，本公开涉及这些化合物在医药或兽医学中的用途，特别是预防或治疗结核病。
• 2-Chloro-4-(trifluoromethyl)pyrimidine-5-<i>N</i>-(3‘,5‘-bis(trifluoromethyl)phenyl)- carboxamide:  A Potent Inhibitor of NF-κB- and AP-1-Mediated Gene Expression Identified Using Solution-Phase Combinatorial Chemistry
  作者：Robert W. Sullivan、Colin G. Bigam、Paul E. Erdman、Moorthy S. S. Palanki、David W. Anderson、Mark E. Goldman、Lynn J. Ransone、Mark J. Suto

  DOI：10.1021/jm970671g

  日期：1998.2.1

  Described is the identification of a novel series of compounds that blocks the activation of two key transcription factors, AP-1 and NF-kB. These transcription factors regulate the expression of several critical proinflammatory proteins and cytokines and represent attractive targets for drug discovery. Through the use of high throughput screening and solution-phase parallel synthesis, inhibitors of both NF-kB and AP-1 were identified. In subsequent testing, these compounds were also shown to block both IL-2 and IL-8 levels in the same cells. One of the most potent compounds in this series, 28, was active in several animal models of inflammation and immunosuppression, thus validating the importance of AP-1 and NF-kB as potential therapeutic targets. The synthesis and preliminary structure-activity relationships of these compounds is addressed.