ethyl (24Z)-3β-(tert-butyldimethylsilyloxy)cholesta-5,24-dien-26-oate | 1452773-05-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: ethyl (24Z)-3β-(tert-butyldimethylsilyloxy)cholesta-5,24-dien-26-oate
• 英文别名: (24Z)-ethyl-3β-(tert-butyldimethylsilyloxy)-5,24-cholestadien-26-oate；ethyl (Z,6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoate
• CAS: 1452773-05-5
• 化学式: C₃₅H₆₀O₃Si
• 分子量: 556.945
• InChiKey: XVSXWIOJQPDKBO-NCTNCRQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.88
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (24Z)-3β-(tert-butyldimethylsilyloxy)cholesta-5,24-dien-26-oate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到ethyl (24Z)-3β-hydroxycholesta-5,24-dien-26-oate
  参考文献：
  名称：

  Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

  摘要：

  Using 3 beta-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.015
• 作为产物：
  描述：

  (3beta)-3-O-叔-丁基二甲基硅烷基-胆甾-5-烯-3,24-二醇 在 草酰氯 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 ethyl (24Z)-3β-(tert-butyldimethylsilyloxy)cholesta-5,24-dien-26-oate
  参考文献：
  名称：

  Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol

  摘要：

  Using 3 beta-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.015

文献信息

• Cholestenoic acid analogues as inverse agonists of the liver X receptors
  作者：Lautaro D. Alvarez、María V. Dansey、María F. Ogara、Carina I. Peña、René Houtman、Adriana S. Veleiro、Adali Pecci、Gerardo Burton

  DOI：10.1016/j.jsbmb.2020.105585

  日期：2020.5

  concentrated on the development of synthetic analogues able to modulate LXR transcriptional response. In this sense, we have previously found that cholestenoic acid analogues with a modified side chain behave as LXR inverse agonists. To further investigate the structure-activity relationships and to explore how cholestenoic acid derivatives interact with the LXRs, we evaluated the LXR biological activity

  肝X受体（LXR）是被氧化的胆固醇代谢物（氧固醇）激活的依赖配体的转录因子，在脂质代谢的转录控制，胆固醇的运输和炎症反应的调节中起基本作用。在过去的十年中，LXR已成为干预人类代谢疾病的有吸引力的药理学靶标，因此，数项工作集中在开发能够调节LXR转录反应的合成类似物上。从这个意义上讲，我们以前已经发现具有修饰的侧链的胆甾烯酸类似物具有LXR反向激动剂的作用。为了进一步研究构效关系，并探讨胆甾烯酸衍生物如何与LXR相互作用，我们评估了含有C24-C25双键的新类似物的LXR生物活性。此外，进行微阵列分析以评估配体结合后共调节剂募集至重组LXR LBD。同样，常规的和加速的分子动力学模拟被用于获得有关逆激动作用的分子决定簇的见解。由于LXR反向激动剂成为控制LXR活性的非常有前途的候选者，此处所示的胆甾烯酸类似物构成了抑制LXR作用的新的相关甾体支架。应用常规和加速的分子动力学模拟来获得有关逆
• Synthesis and biological activity of (24E)- and (24Z)-26-hydroxydesmosterol
  作者：Ratni Saini、Olga Kataeva、Arndt W. Schmidt、Yuqin Wang、Anna Meljon、William J. Griffiths、Hans-Joachim Knölker

  DOI：10.1016/j.bmc.2013.07.015

  日期：2013.9

  Using 3 beta-hydroxychol-5-en-24-oic acid (4) as starting material, the diastereoisomeric allylic alcohols (24E)-26-hydroxydesmosterol (2) and (24Z)-26-hydroxydesmosterol (3) have been synthesised in six steps with 67% and 12% overall yield, respectively. Both of these isomers are found in newborn mouse brain where sterol synthesis is high. Unlike desmosterol (1), neither of these isomers is a ligand to the liver x receptors and thus represents a novel biological deactivation mechanism avoiding cholesterol synthesis. (C) 2013 Elsevier Ltd. All rights reserved.