(2-(Bis-(4-fluorophenyl)methyl)-4-trifluoromethanesulfonyloxythiazol-5-yl)acetic acid | 939437-25-9

• 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: (2-(Bis-(4-fluorophenyl)methyl)-4-trifluoromethanesulfonyloxythiazol-5-yl)acetic acid
• 英文别名: 2-[2-[Bis(4-fluorophenyl)methyl]-4-(trifluoromethylsulfonyloxy)-1,3-thiazol-5-yl]acetic acid；2-[2-[bis(4-fluorophenyl)methyl]-4-(trifluoromethylsulfonyloxy)-1,3-thiazol-5-yl]acetic acid
• CAS: 939437-25-9
• 化学式: C₁₉H₁₂F₅NO₅S₂
• 分子量: 493.432
• InChiKey: XRFAPONFNXIEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2-(Bis-(4-fluorophenyl)methyl)-4-trifluoromethanesulfonyloxythiazol-5-yl)acetic acid 、 3-呋喃硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 2-(2-(Bis(4-fluorophenyl)methyl)-4-(furan-3-yl)thiazol-5-yl)acetic acid
  参考文献：
  名称：

  Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 2

  摘要：

  Structure-activity relationships have been established by exploring the eastern and western side of 5-thiazolyleacetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Benzhydryl motifs in the 2-position of the thiazole was found to be most advantageous. The 4-thiazole position should either carry 3- or 4-fluorophenyl rings or a 4-pyridyl suitably substituted in the flanking 2-position. Several compounds with single digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained. The compound series display a good PK profile and selectivity over a large number of other targets. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.015
• 作为产物：
  描述：

  (2-(Bis-(4-fluorophenyl)methyl)-4-hydroxythiazol-5-yl)acetic acid 、 三氟甲磺酸酐 以 二氯甲烷 为溶剂， 反应 4.0h， 以54%的产率得到(2-(Bis-(4-fluorophenyl)methyl)-4-trifluoromethanesulfonyloxythiazol-5-yl)acetic acid
  参考文献：
  名称：

  WO2007/62677

  摘要：

  公开号：

文献信息

• WO2007/62677
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] THIAZOLYL- AND PYRIMIDINYL-ACETIC ACIDS AND THEIR USE AS CRTH2 RECEPTOR LIGANDS<br/>[FR] ACIDES THIAZOLYL ET PYRIMIDINYL-ACETIQUES ET LEURS UTILISATIONS COMME LIGANDS DU RECEPTEUR CRTH2
  申请人：7TM PHARMA AS

  公开号：WO2007062677A1

  公开（公告）日：2007-06-07

  [EN] [2-[Bis-(4-fluoro-phenyl)methyl]-4-(2-methylpyridin-4-yl)thiazol-5-yl]acetic acid, 4-(2­aminopyridin-4-yl)-2-[bis-(4-fluorophenyl)methyl]thiazol-5-yl}acetic acid, [2-[bis-(4-fluoro­phenyl)-methyl]-4-(3-fluoro-phenyl)-pyrimidin-5-yl]acetic acid, and salts, hydrates and solvates thereof are ligands of the CRTH2 receptor, and of value for the treatment of, inter alia, asthma, rhinitis, allergic airway syndrome, or allergic rhinobronchitis.
  [FR] Acide [2-[Bis-(4-fluoro-phényl)méthyl]-4-(2-méthylpyridin-4-yl)thiazol-5-yl]acétique, acide 4-(2-aminopyridin-4-yl)-2-[bis-(4-fluorophényl)méthyl]thiazol-5-yl}acétique, acide [2-[bis-(4-fluoro-phényl)-méthyl]-4-(3-fluoro-phényl)-pyrimidin-5-yl]acétique, y compris leurs sels, hydrates et solvates, à la fois comme ligands du récepteur CRTH2, et comme produits utiles pour le traitement, entre autres, de l'asthme, de la rhinite, du syndrome allergique des voies respiratoires, ou de la rhino-bronchite allergique.
• Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 2
  作者：Marie Grimstrup、Øystein Rist、Jean-Marie Receveur、Thomas M. Frimurer、Trond Ulven、Jesper M. Mathiesen、Evi Kostenis、Thomas Högberg

  DOI：10.1016/j.bmcl.2009.12.015

  日期：2010.2

  Structure-activity relationships have been established by exploring the eastern and western side of 5-thiazolyleacetic acids as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Benzhydryl motifs in the 2-position of the thiazole was found to be most advantageous. The 4-thiazole position should either carry 3- or 4-fluorophenyl rings or a 4-pyridyl suitably substituted in the flanking 2-position. Several compounds with single digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained. The compound series display a good PK profile and selectivity over a large number of other targets. (C) 2009 Elsevier Ltd. All rights reserved.