4-(3-Chloro-phenyl)-6-phenyl-pyridin-2-ol | 143969-06-6

• 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-(3-Chloro-phenyl)-6-phenyl-pyridin-2-ol
• 英文别名: 4-(3-chlorophenyl)-6-phenyl-1H-pyridin-2-one
• CAS: 143969-06-6
• 化学式: C₁₇H₁₂ClNO
• 分子量: 281.741
• InChiKey: NFZUEYPBFREVAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3-Chloro-phenyl)-6-phenyl-pyridin-2-ol 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-<<4-(3-chlorophenyl)-6-phenyl-2-pyridyl>oxy>-2-methylhexanoic 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：

  1-(氨甲酰甲基)吡啶氯 、 (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 在 sodium hydroxide 、 溶剂黄146 作用下， 生成 4-(3-Chloro-phenyl)-6-phenyl-pyridin-2-ol
  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

• 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
• [EN] SUBSTITUTED BICYCLIC BIS-ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B4 ANTAGONIST ACTIVITY, THEIR PREPARATION AND USE IN PHARMACEUTICAL COMPOSITIONS
  申请人：——

  公开号：WO1992001675A2

  公开（公告）日：1992-02-06

  [FR] L'invention concerne des composés ayant des propriétés antagonistes sélectives sur LTB4 et comprenant un anneau aryle ou hétéroaryle monocyclique ou bicyclique qui possède au moins deux substituants rattachés: (1) un anneau aryle ou hétéroaryle monocyclique ou bicylique substitué ou non substitué et (2) une chaîne de substitution ayant un groupe fonctionnel acide carboxylique terminal ou un dérivé de celui-ci rattaché à la chaîne. Cette invention concerne en outre des procédés pour la préparation de ces composés ainsi que des compositions thérapeutiques comprenant ledit composé, et des procédés pour le traitement de troubles impliquant une activité induite par un antagoniste LTB4 en utilisant lesdites compositions dans lesquelles les composés sont décrits par la formule générale (I) et leurs sels pharmaceutiquement acceptables.