(3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-1-羟基-1,4,4,6-四甲基-2,3,3a,5,8,8a-六氢薁-5-基]乙基]-2,2,5a,7-四甲基-4,5,6,8,9,9a-六氢-3H-苯并[f]氧杂卓-3,7-二醇 | 78518-73-7

• 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
• 中文名称: (3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-1-羟基-1,4,4,6-四甲基-2,3,3a,5,8,8a-六氢薁-5-基]乙基]-2,2,5a,7-四甲基-4,5,6,8,9,9a-六氢-3H-苯并[f]氧杂卓-3,7-二醇
• 英文名称: Sipholenol A
• 英文别名: Sipholenol-A；(3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-1-hydroxy-1,4,4,6-tetramethyl-2,3,3a,5,8,8a-hexahydroazulen-5-yl]ethyl]-2,2,5a,7-tetramethyl-4,5,6,8,9,9a-hexahydro-3H-benzo[b]oxepine-3,7-diol
• CAS: 78518-73-7
• 化学式: C₃₀H₅₂O₄
• 分子量: 476.74
• InChiKey: LVWWPNAIMBYRKG-KOHQYJKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-1-羟基-1,4,4,6-四甲基-2,3,3a,5,8,8a-六氢薁-5-基]乙基]-2,2,5a,7-四甲基-4,5,6,8,9,9a-六氢-3H-苯并[f]氧杂卓-3,7-二醇 在 jones reagent 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.67h， 生成 Sipholenone-B
  参考文献：
  名称：

  The sipholanes, a novel group of triterpenes from the marine sponge Siphonochalina siphonella

  摘要：

  DOI：

  10.1021/jo00168a029
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以73%的产率得到(3R,5aR,6R,7S,9aR)-6-[2-[(1R,3aR,5S,8aR)-1-羟基-1,4,4,6-四甲基-2,3,3a,5,8,8a-六氢薁-5-基]乙基]-2,2,5a,7-四甲基-4,5,6,8,9,9a-六氢-3H-苯并[f]氧杂卓-3,7-二醇
  参考文献：
  名称：

  The sipholanes, a novel group of triterpenes from the marine sponge Siphonochalina siphonella

  摘要：

  DOI：

  10.1021/jo00168a029

文献信息

• New Triterpenoids from the Red Sea Sponge <i>Siphonochalina</i> <i>s</i><i>iphonella</i>
  作者：Yoel Kashman、Tesfamariam Yosief、Shmuel Carmeli

  DOI：10.1021/np0003950

  日期：2001.2.1

  chemical content of the northern, Gulf of Eilat, to the southern-central, Dahlak archipelago, Red Sea sponge Siphonochalina siphonella. The Dahlak sponge was found to be richer in the more polar triterpenes. Nine new compounds (1-4, 7, 8, 15-17) were isolated and identified, among them two sipholane glycosides, sipholenoside A and B (7 and 8), and one compound, dahabinone A (17), possessing a new skeleton

  在比较北部埃拉特湾与南部中部达尔拉克群岛，红海海绵西虹吸管虹吸管的化学含量时，发现了明显的差异。发现Dahlak海绵富含极性更强的三萜。分离并鉴定了九种新化合物（1-4、7、8、15-17），其中包括两种西坡烷糖苷，西坡胆苷A和B（7和8），以及一种化合物，达哈比酮A（17），具有新的骨架。
• Sipholenol and sipholenone, two new triterpenes from the marine sponge (levi).
  作者：U. Shmueli、S. Carmely、A. Groweiss、Y. Kashman

  DOI：10.1016/s0040-4039(01)92531-6

  日期：1981.1

  Several squalene-derived triterpenes possessing a hitherto unknown ring system were isolated from the Red Sea Sponge, . The structure of one of the new compounds, sipholenol (a), was determined by spectroscopic methods including a full x-ray diffraction analysis.

  从红海海绵中分离出几种具有迄今未知的环系统的角鲨烯衍生的三萜。通过包括全X射线衍射分析在内的分光光度法确定了一种新化合物西酚（a）的结构。
• Compositions and methods for treating conditions related to adrenocortical activity and/or excessive steroid production
  申请人：The Regents of the University of Michigan

  公开号：US10512667B2

  公开（公告）日：2019-12-24

  Provided herein are methods for treating subjects having conditions related to adrenocortical activity and/or excessive steroid production. In particular, provided herein are methods for treating subjects having conditions related to adrenocortical activity and/or excessive steroid production through administration of at least one of the following agents: 1) an agent capable of inhibiting cholesterol efflux related to ABCA1 and/or ABCG1; 2) an agent capable of inhibiting MDR1 related cortisol secretion and/or MDR1 P-glycoprotein multiple drug transporter activity; and 3) an agent capable of inhibiting mitochondrial activity.

  本文提供了治疗与肾上腺皮质活性和/或类固醇分泌过多有关的疾病的方法。特别是，本文提供了通过施用以下至少一种制剂治疗肾上腺皮质活性和/或类固醇分泌过多相关疾病的方法：1）能够抑制与 ABCA1 和/或 ABCG1 相关的胆固醇外流的制剂；2）能够抑制与 MDR1 相关的皮质醇分泌和/或 MDR1 P 糖蛋白多药物转运体活性的制剂；以及 3）能够抑制线粒体活性的制剂。
• COMPOSITIONS AND METHODS FOR TREATING CONDITIONS RELATED TO ADRENOCORTICAL ACTIVITY AND/OR EXCESSIVE STEROID PRODUCTION
  申请人：The Regents of the University of Michigan

  公开号：US20180369321A1

  公开（公告）日：2018-12-27

  Provided herein are methods for treating subjects having conditions related to adrenocortical activity and/or excessive steroid production. In particular, provided herein are methods for treating subjects having conditions related to adrenocortical activity and/or excessive steroid production through administration of at least one of the following agents: 1) an agent capable of inhibiting cholesterol efflux related to ABCA1 and/or ABCG1; 2) an agent capable of inhibiting MDR1 related cortisol secretion and/or MDR1 P-glycoprotein multiple drug transporter activity; and 3) an agent capable of inhibiting mitochondrial activity.
• The sipholanes, a novel group of triterpenes from the marine sponge Siphonochalina siphonella
  作者：Shmuel Carmely、Yoel Kashman

  DOI：10.1021/jo00168a029

  日期：1983.10