3-(4-硝基苯氧基)苯甲酸 | 27237-21-4

• 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-(4-硝基苯氧基)苯甲酸
• 英文名称: 3-(4-nitrophenoxy)benzoic acid
• 英文别名: 3-(4-nitro-phenoxy)-benzoic acid；3-(4-Nitro-phenoxy)-benzoesaeure；4-(3-carboxyphenoxy)-1-nitrobenzene；3-(4'-nitrophenoxy)-benzoic acid
• CAS: 27237-21-4
• 化学式: C₁₃H₉NO₅
• mdl: MFCD00690134
• 分子量: 259.218
• InChiKey: RMCHRSGYGNEWJY-UHFFFAOYSA-N

物化性质

• 熔点：
  183 °C
• 沸点：
  438.0±25.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2918990090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-(4-硝基苯氧基)苯甲酸 在 氯化亚砜 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 3-(4-aminophenoxy)-N,N-dimethylbenzamide
  参考文献：
  名称：

  Life Beyond Kinases: Structure-Based Discovery of Sorafenib as Nanomolar Antagonist of 5-HT Receptors

  摘要：

  Of great interest in recent years has been computationally predicting the novel polypharmacology of drug molecules. Here, we applied an "induced-fit" protocol to improve the homology models of 5-HT2A receptor, and we assessed the quality of these models in retrospective virtual screening. Subsequently, we computationally screened the FDA approved drug molecules against the best induced-fit 5-HT2A models and chose six top scoring hits for experimental assays. Surprisingly, one well-known kinase inhibitor, sorafenib, has shown unexpected promiscuous 5-HTRs binding affinities, K-i = 1959, 56, and 417 nM against 5-HT2A, 5-HT2B, and 5-HT2C, respectively. Our preliminary SAR exploration supports the predicted binding mode and further suggests sorafenib to be a novel lead compound for 5HTR ligand discovery. Although it has been well-known that sorafenib produces anticancer effects through targeting multiple kinases, carefully designed experimental studies are desirable to fully understand whether its "off-target" 5-HTR binding activities contribute to its therapeutic efficacy or otherwise undesirable side effects.

  DOI：

  10.1021/jm300338m
• 作为产物：
  描述：

  3-羟基苯甲酸乙酯 在 lithium hydroxide monohydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-(4-硝基苯氧基)苯甲酸
  参考文献：
  名称：

  Life Beyond Kinases: Structure-Based Discovery of Sorafenib as Nanomolar Antagonist of 5-HT Receptors

  摘要：

  Of great interest in recent years has been computationally predicting the novel polypharmacology of drug molecules. Here, we applied an "induced-fit" protocol to improve the homology models of 5-HT2A receptor, and we assessed the quality of these models in retrospective virtual screening. Subsequently, we computationally screened the FDA approved drug molecules against the best induced-fit 5-HT2A models and chose six top scoring hits for experimental assays. Surprisingly, one well-known kinase inhibitor, sorafenib, has shown unexpected promiscuous 5-HTRs binding affinities, K-i = 1959, 56, and 417 nM against 5-HT2A, 5-HT2B, and 5-HT2C, respectively. Our preliminary SAR exploration supports the predicted binding mode and further suggests sorafenib to be a novel lead compound for 5HTR ligand discovery. Although it has been well-known that sorafenib produces anticancer effects through targeting multiple kinases, carefully designed experimental studies are desirable to fully understand whether its "off-target" 5-HTR binding activities contribute to its therapeutic efficacy or otherwise undesirable side effects.

  DOI：

  10.1021/jm300338m

文献信息

• OMEGA-CARBOXYARYL SUBSTITUTED DIPHENYL UREAS AS RAF KINASE INHIBITORS
  申请人：BAYER CORPORATION

  公开号：US20030207872A1

  公开（公告）日：2003-11-06

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。
• omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
  申请人：BAYER CORPORATION

  公开号：US20030181442A1

  公开（公告）日：2003-09-25

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。
• Inhibition of RAF kinase using quinolyl, isoquinolyl or pyridyl ureas
  申请人：BAYER CORPORATION

  公开号：US20020165394A1

  公开（公告）日：2002-11-07

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及在该疗法中的药物组合物。
• Heteroaryl ureas containing nitrogen hetero-atoms as p38 kinase inhibitors
  申请人：BAYER CORPORATION

  公开号：US20020065296A1

  公开（公告）日：2002-05-30

  This invention relates to the use of a group of heteroaryl ureas containing nitrogen in treating p38 mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用含氮的杂环基脲类化合物治疗 p38 介导的疾病，以及用于该疗法的药物组合物。
• Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
  申请人：BAYER CORPORATION

  公开号：US20030144278A1

  公开（公告）日：2003-07-31

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。