(E)-2-(4-(1-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methoxy)imino)propyl)phenoxy)acetic acid | 1268705-23-2

• 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: (E)-2-(4-(1-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methoxy)imino)propyl)phenoxy)acetic acid
• 英文别名: 2-[4-[(E)-C-ethyl-N-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]carbonimidoyl]phenoxy]acetic acid
• CAS: 1268705-23-2
• 化学式: C₂₃H₂₁F₃N₂O₄S
• 分子量: 478.492
• InChiKey: RUJZKTBQTYHWMO-TURZUDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-羟基苯丙酮 在 lithium hydroxide monohydrate 、 盐酸羟胺 、 sodium acetate 、 potassium carbonate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 (E)-2-(4-(1-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methoxy)imino)propyl)phenoxy)acetic acid
  参考文献：
  名称：

  Effect of structurally constrained oxime–ether linker on PPAR subtype selectivity: Discovery of a novel and potent series of PPAR-pan agonists

  摘要：

  A novel series of thaizole and oxazole containing phenoxy acetic acid derivatives is reported as PPAR-pan agonists. Incorporation of structurally constrained oxime-ether based linker in the chemotype of a potent PPAR delta selective agonist GW-501516 was adapted as designing strategy. In vitro, selected test compounds 12a, 12c, 17a and 18a showed PPAR-pan agonists activities and among these four compounds tested, 12a emerged as highly potent and efficacious compound, while 17a exhibited moderate and balanced PPAR-pan agonistic activity. In vivo, selected test compounds 12a and 17a exhibited significant anti-hyperglycemic and anti-hyperlipidemic activities in relevant animal models. These results support our hypothesis that the introduction of structurally constrained oxime-ether linker between lipophilic tail and acidic head plays an important role in modulating subtype selectivity and subsequently led to the discovery of potent PPAR-pan agonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.023

文献信息

• [EN] OXIMINOPHENOXYALKANOIC ACID AND PHENYLALKANOIC ACID DERIVATIVES<br/>[FR] ACIDE OXYMINOPHÉNOXYALCANOÏQUE ET DÉRIVÉS DE L'ACIDE PHENYLALCANOÏQUE
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2008035359A2

  公开（公告）日：2008-03-27

  [EN] The present invention discloses oximinophenoxyalkanoic acid and phenylalkanoic acid of the general formula (I) their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, methods for their preparation, use of these compounds in medicine and the intermediates involved in their preparation.
  [FR] La présente invention concerne un acide oxyminophénoxyalcanoïque et l'acide phénylalcanoïque de la formule générale (I) leurs formes tautomères, leurs stéréoisomères, leurs sels pharmaceutiquement acceptables, les compositions pharmaceutiques les contenant, leurs procédés de préparation, l'utilisation de ces composés en médicine et les intermédiaires impliqués dans leur préparation.