methyl (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate | 1064009-76-2

• 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 (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate
• CAS: 1064009-76-2
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: PGPIYPKONDJEPW-KLQBPHMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  0.0
• 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：
  3

反应信息

• 作为反应物：
  描述：

  methyl (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoate 生成 (4S,5E,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoic acid
  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：

  二十二碳六烯酸 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 三氯硅烷 、 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 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 39.5h， 生成 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

文献信息

• SYNTHESIS OF RESOLVINS AND INTERMEDIATES, COMPOUNDS PREPARED THEREBY, AND USES THEREOF
  申请人：Rodriguez Ana

  公开号：US20100159540A1

  公开（公告）日：2010-06-24

  Methods are disclosed for the preparation of a new class of lipid mediators known as resolvins, with Resolvin D6 (4,17-dihydroxy-5E,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid) being exemplary. Also disclosed are methods for the efficient synthesis of key intermediates in the preparation of such resolvins, such as isotopically labeled ω-3 fatty acid metabolites, and derivatives and analogs thereof. The invention likewise extends to the intermediates so prepared, and to the resolvins prepared with their use.
• [EN] SYNTHESIS OF RESOLVINS AND INTERMEDIATES, COMPOUNDS PREPARED THEREBY, AND USES THEREOF<br/>[FR] SYNTHÈSE DE RÉSOLVINES ET D'INTERMÉDIAIRES, COMPOSÉS PRÉPARÉS PAR CETTE SYNTHÈSE ET LEURS UTILISATIONS
  申请人：UNIV NEW JERSEY MED

  公开号：WO2008118457A2

  公开（公告）日：2008-10-02

  [EN] Methods are disclosed for the preparation of a new class of lipid mediators known as resolvins, with Resolvin D6 (4,17-dihydroxy-5E,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid) being exemplary. Also disclosed are methods for the efficient synthesis of key intermediates in the preparation of such resolvins, such as isotopically labeled ?-3 fatty acid metabolites, and derivatives and analogs thereof. The invention likewise extends to the intermediates so prepared, and to the resolvins prepared with their use.
  [FR] L'invention concerne des procédés de préparation d'une nouvelle classe de médiateurs lipides nommés résolvines, la résolvine D6 (acide 4,17-dihydroxy-5E,7Z,10Z,13Z,15E,19Z-docosahexaénoïque) en étant un exemple. L'invention concerne également des procédés efficaces de synthèse d'intermédiaires clés pour la préparation de telles résolvines, par exemple les métabolites d'acide gras ?-3 isotopiquement marqués et leurs dérivés et analogues. L'invention concerne également les intermédiaires ainsi préparés et les résolvines préparées en les utilisant.
• 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.