methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-acetoxydocosa-5,7,10,13,16,19-hexaenoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-acetoxydocosa-5,7,10,13,16,19-hexaenoate
• 英文别名: methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-acetyloxydocosa-5,7,10,13,16,19-hexaenoate
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: GBKUBNVEVWTJNR-RZAFJODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二十二碳六烯酸 在 吡啶 、 2,4,6-三甲基吡啶 、 氢氧化钾 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 反应 23.0h， 生成 methyl (5E,7Z,10Z,13Z,16Z,19Z)-4-acetoxydocosa-5,7,10,13,16,19-hexaenoate
  参考文献：
  名称：

  Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents

  摘要：

  To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.074

文献信息

• Synthesis of docosahexaenoic acid derivatives designed as novel PPARγ agonists and antidiabetic agents
  作者：Toshimasa Itoh、Itsuki Murota、Kazuyoshi Yoshikai、Sachiko Yamada、Keiko Yamamoto

  DOI：10.1016/j.bmc.2005.07.074

  日期：2006.1

  To discover novel peroxisome proliferator-activated receptor gamma (PPAR gamma) agonists that Could be used as antidiabetic agents, we designed docosahexacnoic acid (DHA) derivatives (2 and 3), which have a hydrophilic substituent at the C(4)-position, based on the crystal structure of the ligand-binding pocket of PPAR gamma. These compounds were synthesized via iodolactolic as a key intermediate. We found that both DHA derivatives (2 and 3) showed PPAR gamma transactivation higher than, or comparable to, that of pioglitazone, which is a TZD derivative used as an antidiabetic agent. DHA derivatives related to these potent Compounds 2 and 3 were also synthesized to study structure-activity relationships. Furthermore, 4-OH DHA 2, which shows strong PPAR gamma transcriptional activity, was separated as an optically pure form. (c) 2005 Elsevier Ltd. All rights reserved.