3-{2-[5-chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}benzoic acid

• 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: 3-{2-[5-chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}benzoic acid
• 英文别名: 3-(2-(2-(Benzyloxy)-5-chlorophenyl)cyclopent-1-enyl)benzoic acid；3-[2-(5-chloro-2-phenylmethoxyphenyl)cyclopenten-1-yl]benzoic acid
• 化学式: C₂₅H₂₁ClO₃
• 分子量: 404.893
• InChiKey: BHIIXYUVEXKWSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-碘苯甲醚, 在 四(三苯基膦)钯 sodium hydroxide 、 sodium thiomethoxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 甲苯 为溶剂， 生成 3-{2-[5-chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}benzoic acid
  参考文献：
  名称：

  The discovery of 6-[2-(5-chloro-2-{[(2,4-difluorophenyl)methyl]oxy}phenyl)-1-cyclopenten-1-yl]-2-pyridinecarboxylic acid, GW848687X, a potent and selective prostaglandin EP1 receptor antagonist for the treatment of inflammatory pain

  摘要：

  The discovery of a series of selective EP1 receptor antagonists based on a 1,2-diaryleyclopentene template is described. After defining the structural requirements for EP1 potency and selectivity, heterocyclic rings were incorporated to reduce logD and improve in vitro pharmacokinetic properties. The 2,6-substituted pyridines and pyridazines gave an appropriate balance of potency, in vivo pharmacokinetic properties and a low potential for inhibiting a range of CYP450 enzymes. From this series, GW848687X was shown to have an excellent profile in models of inflammatory pain and was selected as a development candidate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.041

文献信息

• [EN] (2-((2-ALKOXY) -PHENYL) -CYCLOPENT-1-ENYL) AROMATIC CARBO AND HETEROCYCLIC ACID AND DERIVATIVES<br/>[FR] ACIDE (2-((2-ALCOXY) -PHENYL) -CYCLOPENT-1-ENYL) AROMATIQUE CARBOCYCLIQUE AND HETEROCYCLIQUE ET SES DERIVES
  申请人：GLAXO GROUP LTD

  公开号：WO2003084917A1

  公开（公告）日：2003-10-16

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: (I) wherein A, R1 , R2 , Rx , R8 , R9 and n are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  式(I)或其药学上可接受的衍生物的化合物：其中A、R1、R2、Rx、R8、R9和n如规范中所定义，一种制备这种化合物的方法，包括这种化合物的药物组合物以及这种化合物在医学上的用途。
• (2-((2-alkoxy)-phenyl)-cyclopent-1enyl) aromatic carbo and heterocyclic acid and derivatives
  申请人：Giblin Paul Gerard Martin

  公开号：US20050239802A1

  公开（公告）日：2005-10-27

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein A, R 1 , R 2 , R x , R 8 , R 9 and n are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  公式（I）的化合物或其药学上可接受的衍生物：其中A，R1，R2，Rx，R8，R9和n如规范中所定义，制备这种化合物的过程，包括这种化合物的制药组合物以及在医学中使用这种化合物的用途。
• (2-((2-alkoxy)-phenyl) -cyclopent-1enyl) aromatic carbo and heterocyclic acid and derivatives
  申请人：Glaxo Group Limited

  公开号：US07232821B2

  公开（公告）日：2007-06-19

  Compounds of formula (I) or a pharmaceutically acceptable derivative thereof: wherein A, R1, R2, Rx, R8, R9 and n are as defined in the specification, a process for the preparation of such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  公式（I）化合物或其药学上可接受的衍生物，其中A，R1，R2，Rx，R8，R9和n的定义如规范中所述，制备这种化合物的过程，包含这种化合物的药物组合物以及在医学上使用这种化合物的用途。
• US7232821B2
  申请人：——

  公开号：US7232821B2

  公开（公告）日：2007-06-19
• The discovery of 6-[2-(5-chloro-2-{[(2,4-difluorophenyl)methyl]oxy}phenyl)-1-cyclopenten-1-yl]-2-pyridinecarboxylic acid, GW848687X, a potent and selective prostaglandin EP1 receptor antagonist for the treatment of inflammatory pain
  作者：Gerard M.P. Giblin、Rino A. Bit、Susan H. Brown、Hélène M. Chaignot、Anita Chowdhury、Iain P. Chessell、Nicholas M. Clayton、Tanya Coleman、Adrian Hall、Beverley Hammond、David N. Hurst、Anton D. Michel、Alan Naylor、Riccardo Novelli、Tiziana Scoccitti、David Spalding、Sac P. Tang、Alex W. Wilson、Rich Wilson

  DOI：10.1016/j.bmcl.2006.10.041

  日期：2007.1

  The discovery of a series of selective EP1 receptor antagonists based on a 1,2-diaryleyclopentene template is described. After defining the structural requirements for EP1 potency and selectivity, heterocyclic rings were incorporated to reduce logD and improve in vitro pharmacokinetic properties. The 2,6-substituted pyridines and pyridazines gave an appropriate balance of potency, in vivo pharmacokinetic properties and a low potential for inhibiting a range of CYP450 enzymes. From this series, GW848687X was shown to have an excellent profile in models of inflammatory pain and was selected as a development candidate. (c) 2006 Elsevier Ltd. All rights reserved.