5-nitro-N-(4-trifluoromethylphenyl)-2-pyridinecarboxamide | 1011244-92-0

• 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: 5-nitro-N-(4-trifluoromethylphenyl)-2-pyridinecarboxamide
• 英文别名: 5-nitro-N-[4-(trifluoromethyl)phenyl]pyridine-2-carboxamide
• CAS: 1011244-92-0
• 化学式: C₁₃H₈F₃N₃O₃
• 分子量: 311.22
• InChiKey: SFNYBTWJXCFGFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-nitro-N-(4-trifluoromethylphenyl)-2-pyridinecarboxamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以64%的产率得到5-amino-N-[4-(trifluoromethyl)phenyl]pyridine-2-carboxamide
  参考文献：
  名称：

  Cyclooxygenase-1-Selective Inhibitors Are Attractive Candidates for Analgesics That Do Not Cause Gastric Damage. Design and in Vitro/in Vivo Evaluation of a Benzamide-Type Cyclooxygenase-1 Selective Inhibitor

  摘要：

  Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4(trifluoromethyl)benzamide (18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1IC(50) = 0.80 +/- 0.05 mu M, COX-2IC(50) = 210 I mu M). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage.

  DOI：

  10.1021/jm701191z
• 作为产物：
  描述：

  2-溴-5-硝基吡啶 在 盐酸 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 45.08h， 生成 5-nitro-N-(4-trifluoromethylphenyl)-2-pyridinecarboxamide
  参考文献：
  名称：

  EP2070908

  摘要：

  公开号：

文献信息

• COMPOUND HAVING BENZAMIDE SKELETON AND CYCLOOXYGENASE (COX-1)-SELECTIVE INHIBITORY ACTIVITY
  申请人：National University Corporation Okayama University

  公开号：EP2070908A1

  公开（公告）日：2009-06-17

  This invention provides a novel COX-1-selective inhibitor. This invention relates to a novel compound represented by the formula below or a salt thereof. This invention also relates to an analgesic agent, an antiinflammatory agent, an antitumor agent, an antiplatelet aggregation agent, and a cyclooxygenase-1-selective inhibitor comprising, as an active ingredient, such compound or salt thereof.

  本发明提供了一种新型 COX-1 选择性抑制剂。本发明涉及下式所代表的新型化合物或其盐。本发明还涉及一种镇痛剂、一种抗炎剂、一种抗肿瘤剂、一种抗血小板聚集剂和一种环氧化酶-1 选择性抑制剂，其有效成分包括这种化合物或其盐。
• COMPOUND WITH BENZAMIDE SKELETON HAVING CYCLOOXYGENASE-1 (COX-1)-SELECTIVE INHIBITORY ACTIVITY
  申请人：KAKUTA Hiroki

  公开号：US20100069443A1

  公开（公告）日：2010-03-18

  This invention provides a novel COX-1-selective inhibitor. This invention relates to a novel compound represented by the formula below or a salt thereof. This invention also relates to an analgesic agent, an antiinflammatory agent, an antitumor agent, an antiplatelet aggregation agent, and a cyclooxygenase-1-selective inhibitor comprising, as an active ingredient, such compound or salt thereof.
• Cyclooxygenase-1-Selective Inhibitors Are Attractive Candidates for Analgesics That Do Not Cause Gastric Damage. Design and in Vitro/in Vivo Evaluation of a Benzamide-Type Cyclooxygenase-1 Selective Inhibitor
  作者：Hiroki Kakuta、Xiaoxia Zheng、Hiroyuki Oda、Shun Harada、Yukio Sugimoto、Kenji Sasaki、Akihiro Tai

  DOI：10.1021/jm701191z

  日期：2008.4.1

  Although cyclooxygenase-1 (COX-1) inhibition is thought to be a major mechanism of gastric damage by nonsteroidal anti-inflammatory drugs (NSAIDs), some COX-1-selective inhibitors exhibit strong analgesic effects without causing gastric damage. However, it is not clear whether their analgesic effects are attributable to COX-1-inhibitory activity or other bioactivities. Here, we report that N-(5-amino-2-pyridinyl)-4(trifluoromethyl)benzamide (18f, TFAP), which has a structure clearly different from those of currently available COX-1-selective inhibitors, is a potent COX-1-selective inhibitor (COX-1IC(50) = 0.80 +/- 0.05 mu M, COX-2IC(50) = 210 I mu M). This compound causes little gastric damage in rats even at an oral dose of 300 mg/kg, though it has an analgesic effect at as low a dose as 10 mg/kg. Our results show that COX-1-selective inhibitors can be analgesic agents without causing gastric damage.
• EP2070908
  申请人：——

  公开号：——

  公开（公告）日：——