α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoic acid | 173100-19-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoic acid
• 英文别名: 2,2-Difluoro-3-hydroxy-3-(pyridin-2-YL)propanoic acid；2,2-difluoro-3-hydroxy-3-pyridin-2-ylpropanoic acid
• CAS: 173100-19-1
• 化学式: C₈H₇F₂NO₃
• 分子量: 203.145
• InChiKey: OMQXOGCGVRGZCE-UHFFFAOYSA-N

物化性质

• 沸点：
  354.9±42.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoic acid 、 10-(aminoacetyl)-8-chloro-10,11-dihydrodibenz<1,4>oxazepine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以78%的产率得到N-[2-(3-chloro-6H-benzo[b][1,4]benzoxazepin-5-yl)-2-oxoethyl]-2,2-difluoro-3-hydroxy-3-pyridin-2-ylpropanamide
  参考文献：
  名称：

  Aminoacetyl Moiety as a Potential Surrogate for Diacylhydrazine Group of SC-51089, a Potent PGE₂ Antagonist, and Its Analogs

  摘要：

  8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE(2) antagonist selective for the EP(1) receptor subtype with antinociceptive activity. During metabolism in cultured rat hepatocytes, SC-51089, which contains a diacylhydrazine moiety, has been shown to release hydrazine. Analogs of SC-51089, in which the diacylhydrazine functionality has been replaced by isosteric and isoelectronic groups, have been synthesized and have been shown to be analgesics and PGE(2) antagonists of the EP(1) subtype. This report discusses the structure-activity relationships within these series.

  DOI：

  10.1021/jm950454k
• 作为产物：
  描述：

  ethyl α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以100%的产率得到α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoic acid
  参考文献：
  名称：

  Aminoacetyl Moiety as a Potential Surrogate for Diacylhydrazine Group of SC-51089, a Potent PGE₂ Antagonist, and Its Analogs

  摘要：

  8-Chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[1-oxo-3-(4-pyridinyl)propyl]hydrazide, monohydrochloride (1, SC-51089) is a functional PGE(2) antagonist selective for the EP(1) receptor subtype with antinociceptive activity. During metabolism in cultured rat hepatocytes, SC-51089, which contains a diacylhydrazine moiety, has been shown to release hydrazine. Analogs of SC-51089, in which the diacylhydrazine functionality has been replaced by isosteric and isoelectronic groups, have been synthesized and have been shown to be analgesics and PGE(2) antagonists of the EP(1) subtype. This report discusses the structure-activity relationships within these series.

  DOI：

  10.1021/jm950454k

文献信息

• Substituted dibenzoxazepine compounds
  申请人：G. D. Searle & Co.

  公开号：US05378840A1

  公开（公告）日：1995-01-03

  The present invention provides dibenzoxazepine compounds of Formula I: ##STR1## which are useful as analgesic agents for the treatment of pain, pharmaceutical compositions comprising a therapeutically-effective amount of a compound of Formula I in combination with a pharmaceutically-acceptable carrier, and a method for eliminating or ameliorating pain in an animal comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.

  本发明提供了一种 Formula I 的二苯并噁唑烷化合物：##STR1##，这些化合物可用作治疗疼痛的止痛剂，包括在药物组合物中含有 Formula I 化合物的治疗有效量与药用载体的药物组合物，以及一种消除或减轻动物疼痛的方法，包括向动物施用 Formula I 化合物的治疗有效量。
• Substituted dibenzoxazepine compounds, pharmaceutical compositions and methods of use
  申请人：G.D. Searle & Co.

  公开号：EP0512400A1

  公开（公告）日：1992-11-11

  The present invention provides dibenzoxazepine compounds of Formula I: which are useful as analgesic agents for the treatment of pain, pharmaceutical compositions comprising a therapeutically-effective amount of a compound of Formula I in combination with a pharmaceutically-acceptable carrier, and a method for eliminating or ameliorating pain in an animal comprising administering a therapeutically-effective amount of a compound of Formula I to the animal.

  本发明提供了式 I 的二苯并氧氮杂卓化合物： 可用作治疗疼痛的镇痛剂；包含治疗有效量的式 I 化合物与药学上可接受的载体的药物组合物；以及消除或改善动物疼痛的方法，该方法包括对动物施用治疗有效量的式 I 化合物。
• SUBSTITUTED DIBENZOXAZEPINE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE
  申请人：G.D. SEARLE & CO.

  公开号：EP0583421A1

  公开（公告）日：1994-02-23
• Substituted dibenzoxazepine compounds, pharmaceutical compositions and use
  申请人：G.D. SEARLE & CO.

  公开号：EP0694546B1

  公开（公告）日：2001-06-06
• US5378840A
  申请人：——

  公开号：US5378840A

  公开（公告）日：1995-01-03