(2E,4E,6Z)-7-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-3-methyl-octa-2,4,6-trienoic acid | 331248-16-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,4E,6Z)-7-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-3-methyl-octa-2,4,6-trienoic acid
• 英文别名: 7-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-3-methyl-octa-2,4,6-trienoic acid；(2E,4E,6Z)-7-[3,5-di(propan-2-yl)-2-(2,2,2-trifluoroethoxy)phenyl]-3-methylocta-2,4,6-trienoic acid
• CAS: 331248-16-9
• 化学式: C₂₃H₂₉F₃O₃
• 分子量: 410.477
• InChiKey: UTRWSQUYKCUPGE-BZIVGMQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-3-(3,5-di-iso-propyl-2-hydroxyphenyl)but-2-en-1-ol 在 N,N-二甲基丙烯基脲 、 lithium hydroxide 、 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 (2E,4E,6Z)-7-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-3-methyl-octa-2,4,6-trienoic acid
  参考文献：
  名称：

  Novel (2E,4E,6Z)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes

  摘要：

  Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.

  DOI：

  10.1021/jm020340q