(R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine | 939426-97-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine
• 英文别名: (1R)-1-(5-chloropyridin-2-yl)-1-[3-fluoro-5-(trifluoromethyl)phenyl]-2-phenylethanamine
• CAS: 939426-97-8
• 化学式: C₂₀H₁₅ClF₄N₂
• 分子量: 394.799
• InChiKey: QBFPQAHWHWSJHT-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 1-[(1R)-1-(5-chloropyridin-2-yl)-1-[3-fluoro-5-(trifluoromethyl)phenyl]-2-phenylethyl]-3-cyclohexylurea
  参考文献：
  名称：

  Identification of a potent and metabolically stable series of fluorinated diphenylpyridylethanamine-based cholesteryl ester transfer protein inhibitors

  摘要：

  A novel series of diphenylpyridylethanamine-based inhibitors of cholesteryl ester transfer protein is described. Optimization of the urea moiety, particularly by incorporation of fluorine, is explored to balance in vitro metabolic stability with CETP potency in the whole plasma assay. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.011
• 作为产物：
  描述：

  1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine 在 chiral SFC 作用下， 以 甲醇 为溶剂， 35.0 ℃ 、10.0 MPa 条件下， 生成 (S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine 、 (R)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine
  参考文献：
  名称：

  Diphenylpyridylethanamine (DPPE) Derivatives as Cholesteryl Ester Transfer Protein (CETP) Inhibitors

  摘要：

  A series of diphenylpyridylethanamine (DPPE) derivatives was identified exhibiting potent CETP inhibition. Replacing the labile ester functionality in the initial lead 7 generated a series of amides and ureas. Further optimization of the DPPE series for potency resulted in the discovery of cyclopentylurea 15d, which demonstrated a reduction in cholesterol ester transfer activity (48% of predose level) in hCETP/apoB-100 dual transgenic mice. The PK profile of 15d was suboptimal, and further optimization of the N-terminus resulted in the discovery of amide 20 with an improved PK profile and robust efficacy in transgenic hCETP/apoB-100 mice and in hamsters. Compound 20 demonstrated no significant changes in either mean arterial blood pressure or heart rate in telemeterized rats despite sustained high exposures.

  DOI：

  10.1021/jm300611v

文献信息

• HETEROCYCLIC CETP INHIBITORS
  申请人：Salvati E. Mark

  公开号：US20070161685A1

  公开（公告）日：2007-07-12

  Compounds of formula Ia and Ib wherein A, B, C and R 1 are described herein.

  式Ia和Ib的化合物 其中A、B、C和R1 如本文所述。
• Heterocyclic CETP inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US07888376B2

  公开（公告）日：2011-02-15

  Compounds of formula Ia and Ib wherein A, B, C and R1 are described herein.

  化合物Ia和Ib的公式如下，其中A、B、C和R1的描述如下。
• US7888376B2
  申请人：——

  公开号：US7888376B2

  公开（公告）日：2011-02-15
• [EN] HETEROCYCLIC CETP INHIBITORS<br/>[FR] INHIBITEURS DE CETP HETEROCYCLIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2007062314A2

  公开（公告）日：2007-05-31

  [EN] Compounds of formula Ia and Ib wherein A, B, C and R₁ are described herein.
  [FR] La présente invention concerne des composés de formules Ia et Ib dans lesquelles A, B, C et R₁ ont les correspondances indiquées dans l'invention.