(8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate

• 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: (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
• 英文别名: (3S,8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate；[(3S,8R,9S,10R,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl] trifluoromethanesulfonate
• 化学式: C₂₆H₄₁F₃O₄SSi
• 分子量: 534.756
• InChiKey: XXAWARXRWOSXSC-FYVXYBBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate 在 盐酸 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 1.67h， 生成 乙酸阿比特龙酯
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF ABIRATERONE AND INTERMEDIATES THEREOF

  摘要：

  本发明提供了用于制备阿比特隆的中间体，以及用于制备阿比特隆及其中间体的方法。中间体包括式（IV）的化合物： 其中R代表一个羟基保护基团。

  公开号：

  US20150005489A1
• 作为产物：
  描述：

  去氢表雄酮 在 咪唑 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 9.0h， 生成 (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate
  参考文献：
  名称：

  双脱氢表雄酮类似物作为潜在的新型抗癌剂的合成和生物学评价

  摘要：

  报告了 13 种皮质抑素 A 类似物对 CDK8 的合成、细胞毒性和抑制作用。这些努力表明，在 17 位具有 6-或 7-异喹啉或 5-吲哚侧链的类似物是最有前途的抗增殖剂。这些化合物在 CEM、HeLa 和 HMEC-1 细胞中显示出有效的细胞毒性作用。所有三种化合物的 IC50 值均小于 10µM。最有趣的 10l 类似物对人真皮微血管内皮细胞系 (HMEC-1) 的 IC50 值为 0.59 µM，明显低于参考标准 2-甲氧基雌二醇。在 50 nM 的浓度下，最有效的 10 小时化合物将 CDK8 的活性降低到 35%。

  DOI：

  10.3390/molecules25133052

文献信息

• Synthesis and Biological Evaluation of Analogs of Didehydroepiandrosterone as Potential New Anticancer Agents
  作者：Eirik J. Solum、Sandra Liekens、Trond Vidar Hansen

  DOI：10.3390/molecules25133052

  日期：——

  The synthesis, cytotoxicity and inhibition of CDK8 by thirteen analogs of cortistatin A are reported. These efforts revealed that the analogs with either a 6- or 7-isoquinoline or 5-indole side chain in the 17-position are the most promising anti-proliferative agents. These compounds showed potent cytotoxic effects in CEM, HeLa and HMEC-1 cells. All three compounds exhibited IC50 values < 10µM. The

  报告了 13 种皮质抑素 A 类似物对 CDK8 的合成、细胞毒性和抑制作用。这些努力表明，在 17 位具有 6-或 7-异喹啉或 5-吲哚侧链的类似物是最有前途的抗增殖剂。这些化合物在 CEM、HeLa 和 HMEC-1 细胞中显示出有效的细胞毒性作用。所有三种化合物的 IC50 值均小于 10µM。最有趣的 10l 类似物对人真皮微血管内皮细胞系 (HMEC-1) 的 IC50 值为 0.59 µM，明显低于参考标准 2-甲氧基雌二醇。在 50 nM 的浓度下，最有效的 10 小时化合物将 CDK8 的活性降低到 35%。
• A facile generation of enolates from silyl enol ethers by potassium ethoxide
  作者：Wensheng Yu、Zhendong Jin

  DOI：10.1016/s0040-4039(00)01970-5

  日期：2001.1

  Cyclic silyl enol ethers were successfully cleaved by EtOK to generate the corresponding enolates. Reactions with EtOK; were faster and the corresponding enolates could be trapped by electrophiles and oxidants to give the kinetic products exclusively. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Selective inhibition of the cellular sodium pump by emicymarin and 14ß anhydroxy bufadienolides
  作者：Philip J. Hilton、William McKinnon、Edward C. Gravett、Jean-Marie R. Peron、Christopher M. Frampton、M. Gary Nicholls、Gwyn Lord

  DOI：10.1016/j.steroids.2010.07.010

  日期：2010.12

  Partial inhibition of the sodium pump (Na/K-ATP-ase) by a circulating inhibitor is known to occur in humans. The objectives of this study were to determine the effects of novel bufadienolides lacking an oxygen at C14 on sodium pumps in human erythrocytes and leucocytes, dog kidney and pig brain and to document the importance of the stereochemistry at C17 on the ability to inhibit these sodium pumps. 14 alpha bufadienolides were weak inhibitors of all preparations studied. 3 beta-OH,5 beta,14 beta bufadienolide produced near-total inhibition of dog kidney and pig brain Na/K-ATP-ase. Over the same concentration range, it maximally inhibited the sodium pump of erythrocytes by 70% and leucocytes by 47%. The inhibition profile induced in the leucocyte sodium pump deviated significantly from the simple sigmoidal relationship present in the other preparations over the 3 x 10(-5) to 1 x 10(-7) mol/1 concentration range. Allo-emicymarin (17 alpha) was confirmed to be a weak inhibitor of the sodium pump/ATP-ase compared with emicymarin (17 beta) but both were weaker inhibitors of the leucocyte sodium pump than that of the other preparations. Molecules with the C14 in the beta configuration are more efficacious than in the a configuration. In the case of emicymarin, the attachment of the furone at C17 in the a configuration results in substantially weaker inhibitory activity than in the beta configuration, seen in most cardenolides and bufadienolides. Unlike ouabain and bufalin that show no specificity of action in these preparations, 3 beta-OH,5 beta,14 beta bufadienolide selectively inhibits the activity of at least one low-prevalence subset of the leucocyte Na/K-ATP-ase. (C) 2010 Elsevier Inc. All rights reserved.
• A Suzuki coupling approach to bufadienolides
  作者：Edward C Gravett、Philip J Hilton、Keith Jones、Fernando Romero

  DOI：10.1016/s0040-4039(01)01980-3

  日期：2001.12

  A high yielding route to bufadienolide type steroids using a novel Suzuki Coupling reaction between a range of steroid vinyl triflates and 2-pyrone-5-boronate 11 is presented. (C) 2001 Elsevier Science Ltd. All rights reserved.
• PROCESS FOR THE PREPARATION OF ABIRATERONE AND INTERMEDIATES THEREOF
  申请人：ScinoPharm Taiwan, LTD.

  公开号：US20150005489A1

  公开（公告）日：2015-01-01

  The present invention provides intermediates for preparing abiraterone, and processes for preparing abiraterone and intermediates thereof. The intermediates include a compound of formula (IV): wherein R represents a hydroxy-protecting group.

  本发明提供了用于制备阿比特隆的中间体，以及用于制备阿比特隆及其中间体的方法。中间体包括式（IV）的化合物： 其中R代表一个羟基保护基团。