methyl (4S,7Z,10Z,13Z,16Z,19Z)-4-{[({[(1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyl}amino)carbonyl]oxy}-docosa-5,7,10,13,16,19-hexaenoate | 845673-94-1

• 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: methyl (4S,7Z,10Z,13Z,16Z,19Z)-4-{[({[(1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyl}amino)carbonyl]oxy}-docosa-5,7,10,13,16,19-hexaenoate
• CAS: 845673-94-1
• 化学式: C₄₄H₆₃NO₄
• 分子量: 669.989
• InChiKey: ASKAXERJCWJTQS-RRXGTMLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.18
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,7Z,10Z,13Z,16Z,19Z)-4-{[({[(1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyl}amino)carbonyl]oxy}-docosa-5,7,10,13,16,19-hexaenoate 在 三氯硅烷 、 三乙胺 作用下， 以 苯 为溶剂， 反应 2.5h， 以61%的产率得到methyl (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-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
• 作为产物：
  描述：

  4-hydroxy,5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid γ-lactone 在 4-二甲氨基吡啶 、 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 methyl (4S,7Z,10Z,13Z,16Z,19Z)-4-{[({[(1R,4aS)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methyl}amino)carbonyl]oxy}-docosa-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