N-(5-硝基-2-吡啶基)-4-三氟甲基苯甲酰胺 | 1011244-91-9

• 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: N-(5-硝基-2-吡啶基)-4-三氟甲基苯甲酰胺
• 英文名称: N-(5-nitro-2-pyridyl)-4-trifluoromethylbenzamide
• 英文别名: N-(5-nitropyridin-2-yl)-4-(trifluoromethyl)benzamide；N-(5-Nitro-2-pyridyl)-4-(trifluoromethyl)benzamide
• CAS: 1011244-91-9
• 化学式: C₁₃H₈F₃N₃O₃
• 分子量: 311.22
• InChiKey: IMRLYMRNFSWPBL-UHFFFAOYSA-N

物化性质

• 沸点：
  356.0±42.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)

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：

  N-(5-硝基-2-吡啶基)-4-三氟甲基苯甲酰胺 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以70%的产率得到N-(5-amino-2-pyridinyl)-4-trifluoromethylbenzamide
  参考文献：
  名称：

  EP2070908

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 、 4-(三氟甲基)苯甲酰胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以92%的产率得到N-(5-硝基-2-吡啶基)-4-三氟甲基苯甲酰胺
  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

文献信息

• EP2070908
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• [EN] CARBONOHYDRAZONOYL DICYANIDE COMPOUND INCLUDING AT LEAST TWO TYPES OF ARYL OR HETEROARYL LINKED BY NOVEL LINKER, AND USE THEREOF<br/>[FR] COMPOSÉ DE CARBONOHYDRAZONOYL DICYANIDE COMPRENANT AU MOINS DEUX TYPES D'ARYLE OU D'HÉTÉROARYLE LIÉS PAR UN NOUVEAU LIEUR, ET SON UTILISATION<br/>[KO] 신규한 링커로 결합된 2종 이상의 아릴 또는 헤테로아릴을 포함하는 카르보노하이드라조노일 디시아나이드 화합물 및 이의 용도
  申请人：KOREA INST SCI & TECH

  公开号：WO2021256902A1

  公开（公告）日：2021-12-23

  본 발명은 신규한 링커로 결합된 2종 이상의 아릴 또는 헤테로아릴을 포함하는 카르보노하이드라조노일 디시아나이드 화합물 및 이의 용도에 관한 것이다.
• 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.