ethyl 2-bromo-2-(4-phenylnaphthalen-1-yl)acetate | 1228298-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: ethyl 2-bromo-2-(4-phenylnaphthalen-1-yl)acetate
• CAS: 1228298-52-9
• 化学式: C₂₀H₁₇BrO₂
• 分子量: 369.258
• InChiKey: GWVVUOAFYBVVNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromo-2-(4-phenylnaphthalen-1-yl)acetate 、 2-Thiobarbituric acid 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到ethyl 2-(4,6-dihydroxypyrimidin-2-ylthio)-2-(4-phenylnaphthalen-1-yl)acetate
  参考文献：
  名称：

  Rational design of a pirinixic acid derivative that acts as subtype-selective PPARγ modulator

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) is involved in glucose and lipid homeostasis. PPAR gamma agonists are in clinical use for the treatment of type 2 diabetes. Lately, a new class of selective PPAR gamma modulators (SPPAR gamma Ms) was developed, which are believed to show less side effects than full PPAR gamma agonists. We have previously shown that alpha-substitution of pirinixic acid, a moderate agonist of PPAR alpha and PPAR gamma, leads to low micromolar active balanced dual agonists of PPAR alpha and PPAR alpha. Herein we present modifications of pirinixic acid leading to subtype-selective PPAR gamma agonists and furthermore the development of a selective PPAR gamma modulator guided by molecular docking studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.008
• 作为产物：
  描述：

  ethyl 2-(4-phenylnaphthalen-1-yl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以96%的产率得到ethyl 2-bromo-2-(4-phenylnaphthalen-1-yl)acetate
  参考文献：
  名称：

  Rational design of a pirinixic acid derivative that acts as subtype-selective PPARγ modulator

  摘要：

  Peroxisome proliferator-activated receptor gamma (PPAR gamma) is involved in glucose and lipid homeostasis. PPAR gamma agonists are in clinical use for the treatment of type 2 diabetes. Lately, a new class of selective PPAR gamma modulators (SPPAR gamma Ms) was developed, which are believed to show less side effects than full PPAR gamma agonists. We have previously shown that alpha-substitution of pirinixic acid, a moderate agonist of PPAR alpha and PPAR gamma, leads to low micromolar active balanced dual agonists of PPAR alpha and PPAR alpha. Herein we present modifications of pirinixic acid leading to subtype-selective PPAR gamma agonists and furthermore the development of a selective PPAR gamma modulator guided by molecular docking studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.008