3-硝基-5-(三氟甲基)苯甲酸乙酯 | 203513-22-8

• 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: 3-硝基-5-(三氟甲基)苯甲酸乙酯
• 英文名称: ethyl 5-(trifluoromethyl)-3-nitrobenzoate
• 英文别名: Ethyl 3-nitro-5-(trifluoromethyl)benzoate
• CAS: 203513-22-8
• 化学式: C₁₀H₈F₃NO₄
• 分子量: 263.173
• InChiKey: SHUPMSKIJLRXGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-硝基-5-(三氟甲基)苯甲酸乙酯 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 ethyl 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 3-硝基-5-(三氟甲基)苯甲酸乙酯
  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

• Reaction of Nitroorganic Compounds Using Thiourea Catalysts Anchored to Polymer Support
  作者：Yoshiji Takemoto、Hideto Miyabe、Sayo Tuchida、Masashige Yamauchi

  DOI：10.1055/s-2006-950196

  日期：——

  Immobilization of chiral thiourea catalyst was studied. The PEG-bound thiourea showed better catalytic activity than those of the carboxypolystyrene HL resin-bound and TentaGel carboxy resin-bound thioureas. In the presence of PEG-bound thiourea, Michael and tandem Michael reactions of trans-β-nitrostyrene proceeded enantioselectively.

  研究了手性硫脲催化剂的固定化。与羧基聚苯乙烯 HL 树脂和 TentaGel 羧基树脂结合的硫脲相比，PEG 结合的硫脲显示出更好的催化活性。在 PEG 结合型硫脲存在的情况下，反式-δ-硝基苯乙烯的迈克尔反应和串联迈克尔反应可进行对映选择性反应。
• 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.