4-phenyl-6-[4-(trifluoromethyl)phenyl]-1H-pyridin-2-one | 143969-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-phenyl-6-[4-(trifluoromethyl)phenyl]-1H-pyridin-2-one
• CAS: 143969-11-3
• 化学式: C₁₈H₁₂F₃NO
• 分子量: 315.295
• InChiKey: NASWUMKSLZQERB-UHFFFAOYSA-N

物化性质

• 沸点：
  498.2±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-phenyl-6-[4-(trifluoromethyl)phenyl]-1H-pyridin-2-one 在 氢氧化钾 、 silver carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 6-<<6-<4-(trifluoromethyl)phenyl>-4-phenyl-2-pyridyl>oxy>hexanoic acid
  参考文献：
  名称：

  .omega.-[(4,6-Diphenyl-2-pyridyl)oxy]alkanoic acid derivatives: a new family of potent and orally active LTB4 antagonists

  摘要：

  A series of omega-[(4,6-diphenyl-2-pyridyl)oxy]alkanoic acid derivatives was prepared which inhibited the binding of leukotriene B4 to its receptors on guinea pig spleen membranes and on human polymorphonuclear leukocytes (PMNs) and selectively antagonized the LTB4-induced elastase release in human PMNs. On the basis of these three screens, a structure-activity relationship was investigated. Alpha-Substitution on the carboxylic acid side chain led to only small changes in the binding affinities but greatly enhanced the LTB4 antagonist activity. Substitution on the phenyl rings was also evaluated. The terminal carboxylic acid function can be replaced by a tetrazole ring without loss in activity. The beat in vitro LTB4 antagonists of this series were investigated in vivo in the inhibition of LTB4-induced leukopenia in rabbits. Compound 9b (RP69698) displayed potent LTB4 antagonist activity, after oral administration, with an ED50 value of 6.7 mg/kg.

  DOI：

  10.1021/jm00101a008
• 作为产物：
  描述：

  trans-4'-(trifluoromethyl)chalcone 、 1-(氨甲酰甲基)吡啶氯 在 sodium hydroxide 、 溶剂黄146 作用下， 生成 4-phenyl-6-[4-(trifluoromethyl)phenyl]-1H-pyridin-2-one
  参考文献：
  名称：

  .omega.-[(4,6-Diphenyl-2-pyridyl)oxy]alkanoic acid derivatives: a new family of potent and orally active LTB4 antagonists

  摘要：

  A series of omega-[(4,6-diphenyl-2-pyridyl)oxy]alkanoic acid derivatives was prepared which inhibited the binding of leukotriene B4 to its receptors on guinea pig spleen membranes and on human polymorphonuclear leukocytes (PMNs) and selectively antagonized the LTB4-induced elastase release in human PMNs. On the basis of these three screens, a structure-activity relationship was investigated. Alpha-Substitution on the carboxylic acid side chain led to only small changes in the binding affinities but greatly enhanced the LTB4 antagonist activity. Substitution on the phenyl rings was also evaluated. The terminal carboxylic acid function can be replaced by a tetrazole ring without loss in activity. The beat in vitro LTB4 antagonists of this series were investigated in vivo in the inhibition of LTB4-induced leukopenia in rabbits. Compound 9b (RP69698) displayed potent LTB4 antagonist activity, after oral administration, with an ED50 value of 6.7 mg/kg.

  DOI：

  10.1021/jm00101a008

文献信息

• Consecutive Alkynylation–Michael Addition–Cyclocondensation (AMAC) Multicomponent Syntheses of α-Pyrones and α-Pyridones
  作者：Thomas Müller、Natascha Breuer

  DOI：10.1055/s-0037-1610129

  日期：2018.7

  Abstract A novel consecutive three-component synthesis of α-pyrones is based upon an alkynylation–Michael addition–cyclocondensation (AMAC) sequence, starting from (hetero)aroyl chloride and terminal alkyne to furnish the alkynone which reacts with malonates to give the α-pyrones in moderate to very good yields. By concatenating ammonolysis of the α-pyrones, an alkynylation–Michael addition–cyclocon

  摘要 一种新颖的连续三组分合成α-吡喃酮的方法是基于炔基化-迈克尔加成-环缩合（AMAC）序列，从（杂）芳酰氯和末端炔烃开始，提供炔基，与丙二酸酯反应生成α-吡喃酮。中等至非常高的产量。通过串联α-吡喃酮的氨解，可以构想α-吡啶酮的炔基化-迈克尔加成-环缩合-氨解（AMACA）合成。具有和不具有酯官能度的α-吡啶酮产物以中等收率获得。 一种新颖的连续三组分合成α-吡喃酮的方法是基于炔基化-迈克尔加成-环缩合（AMAC）序列，从（杂）芳酰氯和末端炔烃开始，提供炔基，与丙二酸酯反应生成α-吡喃酮。中等至非常高的产量。通过串联α-吡喃酮的氨解，可以构想α-吡啶酮的炔基化-迈克尔加成-环缩合-氨解（AMACA）合成。具有和不具有酯官能度的α-吡啶酮产物以中等收率获得。
• Labaudiniere Richard, Dereu Norbert, Cavy Francoise, Guillet Marie-Christ+, J. Med. Chem., 35 (1992) N 23, S 4315-4324
  作者：Labaudiniere Richard, Dereu Norbert, Cavy Francoise, Guillet Marie-Christ+

  DOI：——

  日期：——
• SUBSTITUTED BICYCLIC BIS-ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B 4? ANTAGONIST ACTIVITY, THEIR PREPARATION AND USE IN PHARMACEUTICAL COMPOSITIONS
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0540604A1

  公开（公告）日：1993-05-12
• US5366982A
  申请人：——

  公开号：US5366982A

  公开（公告）日：1994-11-22
• US5492915A
  申请人：——

  公开号：US5492915A

  公开（公告）日：1996-02-20