N-(4,6-dimethylpyridin-2-yl)-3-(trifluoromethyl)benzamide | 94843-62-6

• 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: N-(4,6-dimethylpyridin-2-yl)-3-(trifluoromethyl)benzamide
• CAS: 94843-62-6
• 化学式: C₁₅H₁₃F₃N₂O
• 分子量: 294.276
• InChiKey: XUPWUVGDTFDMHB-UHFFFAOYSA-N

物化性质

• 熔点：
  82 °C(Solv: hexane (110-54-3))
• 沸点：
  312.9±42.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4,6-dimethylpyridin-2-yl)-3-(trifluoromethyl)benzamide 、 碘甲烷 在 碳酸氢钠 作用下， 生成 3-Trifluoromethyl-N-[1,4,6-trimethyl-1H-pyridin-(2E)-ylidene]-benzamide
  参考文献：
  名称：

  Non-acidic antiinflammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives

  摘要：

  Benzamides I, phenylalkanamides II and cinnamamides III are structurally related to the antiinflammatory N-(4,6-dimethylpyridin-2-yl)benzamide 1. These were synthesized and the transformation of the 2-aminopyridine nucleus of benzamides I into a 2-imino-1,2-dihydropyridine structure (compounds IV) was also carried out. Of the 49 new derivatives, the 3-fluorobenzamide 9 was the most potent in the oral treatment of carrageenen-induced peripheral edema; IC50 = 12.2 mg.kg(-1). It was 3 times as active as benzamide 1, but the latter nevertheless had a better therapeutic index (LD(50)/IC50) of 52 against 23. Benzamide 1, a non-acidic antiinflammatory compound devoid of any blocking activity on cyclooxygenase, markedly reduces the production of reactive oxygen species in rat peritoneal macrophages. This compound probably acts at the membrane, perhaps by interference with transmembrane events.

  DOI：

  10.1016/0223-5234(94)90107-4
• 作为产物：
  描述：

  2-氨基-4,6-二甲基吡啶 、 3-(三氟甲基)苯甲酰氯 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以54%的产率得到N-(4,6-dimethylpyridin-2-yl)-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  N-（4,6-二甲基-2-吡啶基）苯甲酰胺的合成及其中心多巴胺能作用。

  摘要：

  合成了N-（4,6-二甲基-2-吡啶基）苯甲酰胺1-24和相应的三级衍生物29-33，并通过测试它们对幼稚和再固定化小鼠运动的影响来研究其对多巴胺的抑制作用。与原丙酰胺不同，它们没有显示出任何抗多巴胺能的特性，但是一些二级衍生物反而显示了突触后多巴胺能激动作用。随后研究了后一种化合物对利血平诱导的运动障碍的阿扑吗啡逆转以及对大鼠脑HVA水平的影响。化合物11在6-羟基多巴胺损伤的小鼠中引起的相反盘旋表明涉及直接机制。

  DOI：

  10.1021/jm50001a004

文献信息

• BOUHAYAT, SAID;PIESSARD, S.;LE, BAUT, G.;SPARFEL, L.;PETIT, J. -Y.;PIRIOU+, J. MED. CHEM., 1985, 28, N 5, 555-559
  作者：BOUHAYAT, SAID、PIESSARD, S.、LE, BAUT, G.、SPARFEL, L.、PETIT, J. -Y.、PIRIOU+

  DOI：——

  日期：——
• Non-acidic antiinflammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives
  作者：J ROBERT、S ROBERTPIESSARD、M DUFLOS、G LEBAUT、E KHETTAB、N GRIMAUD、J PETIT、L WELIN

  DOI：10.1016/0223-5234(94)90107-4

  日期：——

  Benzamides I, phenylalkanamides II and cinnamamides III are structurally related to the antiinflammatory N-(4,6-dimethylpyridin-2-yl)benzamide 1. These were synthesized and the transformation of the 2-aminopyridine nucleus of benzamides I into a 2-imino-1,2-dihydropyridine structure (compounds IV) was also carried out. Of the 49 new derivatives, the 3-fluorobenzamide 9 was the most potent in the oral treatment of carrageenen-induced peripheral edema; IC50 = 12.2 mg.kg(-1). It was 3 times as active as benzamide 1, but the latter nevertheless had a better therapeutic index (LD(50)/IC50) of 52 against 23. Benzamide 1, a non-acidic antiinflammatory compound devoid of any blocking activity on cyclooxygenase, markedly reduces the production of reactive oxygen species in rat peritoneal macrophages. This compound probably acts at the membrane, perhaps by interference with transmembrane events.
• Synthesis and Central Dopaminergic Effects of N-(4,6-Dimethyl-2-pyridinyl)benzamides
  作者：Saïd Bouhayat、Sylvie Piessard、Guillaume Le Baut、Louis Sparfel、Jean-Yves Petit、François Piriou、Lucien Welin

  DOI：10.1021/jm50001a004

  日期：1985.5

  N-(4,6-Dimethyl-2-pyridinyl)benzamides 1-24 and the corresponding tertiary derivatives 29-33 were synthesized and studied for possible dopamine-inhibitory properties by testing their effect on motility of naive and reserpinized mice. Unlike the orthopramides, they failed to show any antidopaminergic properties, but some of the secondary derivatives showed instead effects of postsynaptic dopaminergic

  合成了N-（4,6-二甲基-2-吡啶基）苯甲酰胺1-24和相应的三级衍生物29-33，并通过测试它们对幼稚和再固定化小鼠运动的影响来研究其对多巴胺的抑制作用。与原丙酰胺不同，它们没有显示出任何抗多巴胺能的特性，但是一些二级衍生物反而显示了突触后多巴胺能激动作用。随后研究了后一种化合物对利血平诱导的运动障碍的阿扑吗啡逆转以及对大鼠脑HVA水平的影响。化合物11在6-羟基多巴胺损伤的小鼠中引起的相反盘旋表明涉及直接机制。