(E)-ethyl 2-(4-(cyclohexyl(hydroxyimino)methyl)-2-methylphenoxy)acetate | 1268705-11-8

• 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)-ethyl 2-(4-(cyclohexyl(hydroxyimino)methyl)-2-methylphenoxy)acetate
• CAS: 1268705-11-8
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: QTFMYAOCBKSDDP-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.12
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 2-(4-(cyclohexyl(hydroxyimino)methyl)-2-methylphenoxy)acetate 在 lithium hydroxide monohydrate 、 水 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (E)-2-(4-(cyclohexyl(((5-methyl-2-phenyloxazol-4-yl)methoxy)imino)methyl)-2-methylphenoxy)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
• 作为产物：
  描述：

  ethyl 2-(4-(cyclohexanecarbonyl)-2-methylphenoxy)acetate 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以66%的产率得到(E)-ethyl 2-(4-(cyclohexyl(hydroxyimino)methyl)-2-methylphenoxy)acetate
  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