ethyl (2E,6E,10E)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoate | 1243216-24-1

• 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: ethyl (2E,6E,10E)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoate
• CAS: 1243216-24-1
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: CXSYYVFOLXESLR-JVRISFDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  23.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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 (2E,6E,10E)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoate 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到(2E,6E,10E)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoic acid
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives

  摘要：

  Synthetic retinoids have generated in the fields of dermatology and oncology due to their potent anti-proliferative and differentiation activities. We efficiently synthesized different demethyl geranylgeranoic acid (GGA) analogs, and evaluated their biological activities. Among the demethyl analogs synthesized, 3-demethyl derivative exhibited the highest anti-proliferative activity in HL-60 cells. In addition, a 3-demethyl derivative induced apoptosis more potently than 9Z-retinoic acid. These activities were due to the high binding affinity of 3-demethyl derivative for retinoid receptors. We found that, in a conjugated polyene system combined with a methyl substituent, the position of the methyl played an important role in the regulation of gene transcription and apoptosis-inducing activity. These results provided useful information on the structure-activity relationships of GGA derivatives that function as acyclic retinoic acid analogs. This information is likely to be useful in the development of new anti-cancer drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.003
• 作为产物：
  描述：

  ethyl (2Z,6E,10E)-11,15-dimethyl-3-(trifluoromethylsulfonyloxy)-2,6,10,14-hexadecatetraenoate 、 四甲基锡 在 copper(l) iodide 、 二(氰基苯)二氯化钯 、 三苯胂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 10.0h， 以92%的产率得到ethyl (2E,6E,10E)-3,11,15-trimethyl-2,6,10,14-hexadecatetraenoate
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives

  摘要：

  Synthetic retinoids have generated in the fields of dermatology and oncology due to their potent anti-proliferative and differentiation activities. We efficiently synthesized different demethyl geranylgeranoic acid (GGA) analogs, and evaluated their biological activities. Among the demethyl analogs synthesized, 3-demethyl derivative exhibited the highest anti-proliferative activity in HL-60 cells. In addition, a 3-demethyl derivative induced apoptosis more potently than 9Z-retinoic acid. These activities were due to the high binding affinity of 3-demethyl derivative for retinoid receptors. We found that, in a conjugated polyene system combined with a methyl substituent, the position of the methyl played an important role in the regulation of gene transcription and apoptosis-inducing activity. These results provided useful information on the structure-activity relationships of GGA derivatives that function as acyclic retinoic acid analogs. This information is likely to be useful in the development of new anti-cancer drugs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.003

文献信息

• The Diterpenoid Substrate Analogue 19‐<i>nor</i>‐GGPP Reveals Pronounced Methyl Group Effects in Diterpene Cyclisations
  作者：Kizerbo A. Taizoumbe、Bernd Goldfuss、Jeroen S. Dickschat

  DOI：10.1002/anie.202318375

  日期：2024.2.5

  te (with a methyl group removed) has been synthesised and converted into diterpene analogues with 20 diterpene synthases. In some cases only the desmethyl derivatives of the natural enzyme products were obtained, but with several enzymes a dramatic change in the reactivity was observed. The newly opened reaction paths to compounds with unknown skeletons reveal an intriguing methyl group effect in diterpene

  已合成 19-正-香叶基香叶基二磷酸（除去甲基）并用 20 个二萜合酶将其转化为二萜类似物。在某些情况下，仅获得了天然酶产品的去甲基衍生物，但观察到几种酶的反应性发生显着变化。新开辟的未知骨架化合物的反应路径揭示了二萜生物合成中有趣的甲基效应。