(1R)-1-[2-fluoro-4-[3-fluoro-2-(trifluoromethyl)phenyl]phenyl]ethanamine | 925215-09-4

• 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: (1R)-1-[2-fluoro-4-[3-fluoro-2-(trifluoromethyl)phenyl]phenyl]ethanamine
• CAS: 925215-09-4
• 化学式: C₁₅H₁₂F₅N
• 分子量: 301.259
• InChiKey: IDYFJOFWSGRSKE-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-1-[2-fluoro-4-[3-fluoro-2-(trifluoromethyl)phenyl]phenyl]ethanamine 在 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 N-[(1R)-1-[2-fluoro-4-[3-fluoro-2-(trifluoromethyl)phenyl]phenyl]ethyl]-1-[(2,2,2-trifluoroacetyl)amino]cyclopropane-1-carboxamide
  参考文献：
  名称：

  Development of Orally Bioavailable and CNS Penetrant Biphenylaminocyclopropane Carboxamide Bradykinin B₁ Receptor Antagonists

  摘要：

  A series of biphenylaminocyclopropane carboxamide based bradykinin B-1 receptor antagonists has been developed that possesses good pharmacokinetic properties and is CNS penetrant. Discovery that the replacement of the trifluoropropionamide in the lead structure with polyhaloacetamides, particularly a trifluoroacetamide, significantly reduced P-glycoprotein mediated efflux for the series proved essential. One of these novel bradykinin B-1 antagonists (13b) also exhibited suitable pharmacokinetic properties and efficient ex vivo receptor occupancy for further development as a novel approach for the treatment of pain and inflammation.

  DOI：

  10.1021/jm061094b
• 作为产物：
  描述：

  4-溴-2-氟苯甲醛 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium diacetate 盐酸 、 potassium acetate 、 4-甲基苯磺酸吡啶 、 magnesium sulfate 、 potassium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 80.5h， 生成 (1R)-1-[2-fluoro-4-[3-fluoro-2-(trifluoromethyl)phenyl]phenyl]ethanamine
  参考文献：
  名称：

  Development of Orally Bioavailable and CNS Penetrant Biphenylaminocyclopropane Carboxamide Bradykinin B₁ Receptor Antagonists

  摘要：

  A series of biphenylaminocyclopropane carboxamide based bradykinin B-1 receptor antagonists has been developed that possesses good pharmacokinetic properties and is CNS penetrant. Discovery that the replacement of the trifluoropropionamide in the lead structure with polyhaloacetamides, particularly a trifluoroacetamide, significantly reduced P-glycoprotein mediated efflux for the series proved essential. One of these novel bradykinin B-1 antagonists (13b) also exhibited suitable pharmacokinetic properties and efficient ex vivo receptor occupancy for further development as a novel approach for the treatment of pain and inflammation.

  DOI：

  10.1021/jm061094b

文献信息

• Development of Orally Bioavailable and CNS Penetrant Biphenylaminocyclopropane Carboxamide Bradykinin B₁ Receptor Antagonists
  作者：Scott D. Kuduk、Christina N. Di Marco、Ronald K. Chang、Michael R. Wood、Kathy M. Schirripa、June J. Kim、Jenny M. C. Wai、Robert M. DiPardo、Kathy L. Murphy、Richard W. Ransom、C. Meacham Harrell、Duane R. Reiss、Marie A. Holahan、Jacquelynn Cook、J. Fred Hess、Nova Sain、Mark O. Urban、Cuyue Tang、Thomayant Prueksaritanont、Douglas J. Pettibone、Mark G. Bock

  DOI：10.1021/jm061094b

  日期：2007.1.1

  A series of biphenylaminocyclopropane carboxamide based bradykinin B-1 receptor antagonists has been developed that possesses good pharmacokinetic properties and is CNS penetrant. Discovery that the replacement of the trifluoropropionamide in the lead structure with polyhaloacetamides, particularly a trifluoroacetamide, significantly reduced P-glycoprotein mediated efflux for the series proved essential. One of these novel bradykinin B-1 antagonists (13b) also exhibited suitable pharmacokinetic properties and efficient ex vivo receptor occupancy for further development as a novel approach for the treatment of pain and inflammation.