N-乙基-2-硝基-N-(苯基)苯甲酰胺 | 328259-21-8

• 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: N-乙基-2-硝基-N-(苯基)苯甲酰胺
• 英文名称: N-ethyl-2-nitro-N-(phenyl)benzamide
• 英文别名: 2-nitro-benzoic acid-(N-ethyl-anilide)；2-Nitro-benzoesaeure-(N-aethyl-anilid)；N-ethyl-2-nitro-N-phenylbenzamide
• CAS: 328259-21-8
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD00592192
• 分子量: 270.288
• InChiKey: UBAIVWQJHUXYKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-乙基-2-硝基-N-(苯基)苯甲酰胺 在 乙醇 、 硫酸 、 铂 、 sodium nitrite 作用下， 生成 5-ethylphenanthridin-6(5H)-one
  参考文献：
  名称：

  Govindachari; Arumugam, Journal Of Scientific and Industrial Research, 1954, vol. 13B, p. 694,697

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硝基-N-苯基苯甲酰胺 、 碘乙烷 在 sodium hydride 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以92%的产率得到N-乙基-2-硝基-N-(苯基)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

• ISATOIC ANHYDRIDE. I. REACTIONS WITH PRIMARY AND SECONDARY AMINES AND WITH SOME AMIDES¹
  作者：ROBERT H. CLARK、E. C. WAGNER

  DOI：10.1021/jo01183a007

  日期：1944.1
• Govindachari; Arumugam, Journal Of Scientific and Industrial Research, 1954, vol. 13B, p. 694,697
  作者：Govindachari、Arumugam

  DOI：——

  日期：——
• 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.