3β-O-acetyl-theonellasterol | 1421231-69-7

• 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: 3β-O-acetyl-theonellasterol
• 英文别名: acetyltheonellasterol；[(3S,5R,9R,10R,13R,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-4-methylidene-1,2,3,5,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1421231-69-7
• 化学式: C₃₂H₅₂O₂
• 分子量: 468.764
• InChiKey: JLSWPWUBFIKCCQ-JNVQAEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸酐 、 theonellasterol 在 吡啶 作用下， 反应 24.0h， 以95%的产率得到3β-O-acetyl-theonellasterol
  参考文献：
  名称：

  来自海绵 Theonella swinhoei 的 4-亚甲基甾醇。

  摘要：

  从海绵 Theonella swinhoei 中分离出三种新的 4-亚甲基甾醇，theonellasterol K (1)、乙酰基theonellasterol (2) 和 acetyldehydroconicasterol (3)，以及两种已知的甾醇，theonellasterol (4) 和 theonellasterone (5)。这些化合物的结构基于它们的光谱数据和核磁共振数据与已知类似物的比较来阐明。化合物 1 对 HCT-116、K562 和 Molt 4 癌细胞系表现出显着的细胞毒活性。

  DOI：

  10.3390/md10071536

文献信息

• Preliminary Structure-Activity Relationship on Theonellasterol, a New Chemotype of FXR Antagonist, from the Marine Sponge Theonella swinhoei
  作者：Valentina Sepe、Raffaella Ummarino、Maria D'Auria、Orazio Taglialatela-Scafati、Simona Marino、Claudio D'Amore、Barbara Renga、Maria Chini、Giuseppe Bifulco、Yoichi Nakao、Nobuhiro Fusetani、Stefano Fiorucci、Angela Zampella

  DOI：10.3390/md10112448

  日期：——

  Using theonellasterol as a novel FXR antagonist hit, we prepared a series of semi-synthetic derivatives in order to gain insight into the structural requirements for exhibiting antagonistic activity. These derivatives are characterized by modification at the exocyclic carbon-carbon double bond at C-4 and at the hydroxyl group at C-3 and were prepared from theonellasterol using simple reactions. Pharmacological investigation showed that the introduction of a hydroxyl group at C-4 as well as the oxidation at C-3 with or without concomitant modification at the exomethylene functionality preserve the ability of theonellasterol to inhibit FXR transactivation caused by CDCA. Docking analysis showed that the placement of these molecules in the FXR-LBD is well stabilized when on ring A functional groups, able to form hydrogen bonds and π interactions, are present.