(8R,9S,13S,14S,17S)-13-Methyl-17-trimethylsilanylethynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | 50866-93-8

• 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,13S,14S,17S)-13-Methyl-17-trimethylsilanylethynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• 英文别名: (8R,9S,13S,14S,17S)-13-methyl-17-(2-trimethylsilylethynyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 50866-93-8
• 化学式: C₂₃H₃₂O₂Si
• 分子量: 368.591
• InChiKey: FRKCCMXXMUCBTL-MHMIHQHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17S)-13-Methyl-17-trimethylsilanylethynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol 在 Pd-BaSO₄ 氢气 作用下， 以 乙醇 为溶剂， 反应 25.0h， 以29%的产率得到(8R,9S,13S,14S,17R)-13-methyl-17-[(Z)-2-trimethylsilylethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Steroidal silicon side-chain analogs as potential antifertility agents

  摘要：

  A number of silicon-substituted analogues of ethynylestradiol that exhibit modified and enhanced biological activities have been synthesized. Particularly noteworthy are a group of [(trialkylsilyl)ethynyl]estradiol analogues that exhibit high antifertility potency and markedly reduced estrogenic activity. The best compounds synthesized are 17 alpha-[(triethylsilyl)ethynyl]estradiol (5) and 17 alpha-[(tert-butyldimethylsilyl)ethynyl]estradiol (33), which show a separation of antifertility from estrogenic activity in the rat. The results of structure-activity studies indicate a good correlation between the observed biological activities and the calculated van der Waals volumes of the three variable silicon substituents.

  DOI：

  10.1021/jm00387a011
• 作为产物：
  描述：

  炔雌醇 在 盐酸 、 甲基溴化镁 作用下， 以 甲醇 、 水 为溶剂， 反应 39.0h， 生成 (8R,9S,13S,14S,17S)-13-Methyl-17-trimethylsilanylethynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Steroidal silicon side-chain analogs as potential antifertility agents

  摘要：

  A number of silicon-substituted analogues of ethynylestradiol that exhibit modified and enhanced biological activities have been synthesized. Particularly noteworthy are a group of [(trialkylsilyl)ethynyl]estradiol analogues that exhibit high antifertility potency and markedly reduced estrogenic activity. The best compounds synthesized are 17 alpha-[(triethylsilyl)ethynyl]estradiol (5) and 17 alpha-[(tert-butyldimethylsilyl)ethynyl]estradiol (33), which show a separation of antifertility from estrogenic activity in the rat. The results of structure-activity studies indicate a good correlation between the observed biological activities and the calculated van der Waals volumes of the three variable silicon substituents.

  DOI：

  10.1021/jm00387a011

文献信息

• The Reversible Nicholas Reaction in the Synthesis of Highly Symmetric Natural-Product-Based Macrocycles
  作者：María C. de la Torre、María Asenjo、Pedro Ramírez-López、Miguel A. Sierra

  DOI：10.1002/ejoc.201403541

  日期：2015.2

  Two different approaches to highly symmetric macrocycles by reversible Nicholas reactions have been developed. The first sequence uses a bis[Co2(CO)6] complex derived from a double propargylic alcohol supporting two natural product moieties. The reactions with BF3·OEt2 and different benzene dimethanols yielded either (1:1) or (2:2) adducts, depending essentially on the nature of the tether joining

  通过可逆尼古拉斯反应开发了两种不同的高度对称大环方法。第一个序列使用衍生自支持两个天然产物部分的双炔丙醇的双 [Co2(CO)6] 复合物。与 BF3·OEt2 和不同苯二甲醇的反应产生 (1:1) 或 (2:2) 加合物，这主要取决于连接两个 Co 簇的系链的性质。或者，与一个类固醇和一个单萜片段以及一个含有醇部分的芳族末端共络合的炔丙醇模板的 Nicholas 反应产生了源自自二聚化的相应大环。两条通往大环的路线是互补的，可以有效地产生复杂的含有天然产物的结构。
• Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF₃
  作者：Shitao Pan、Qiqiang Xie、Xiu Wang、Qian Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/d2cc00975g

  日期：——

  The TMSCF₃-derived CuCF₂CF₃ species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes.

  TMS 衍生的CuCF2CF3物种已成功应用于有机硼酸酯和末端炔烃的五氟乙基化反应。
• Utilizing Estra-1,3,5,16-Tetraene Scaffold: Design and Synthesis of Nitric Oxide Donors as Chemotherapeutic Resistance Combating Agents in Liver Cancer
  作者：Mahrous A. Abou-Salim、Mohamed A. Shaaban、Mohammed K. Abd El Hameid、Mohammed M. Alanazi、Fathi Halaweish、Yaseen A. M. M. Elshaier

  DOI：10.3390/molecules28062754

  日期：——

  A new series of nitric oxide-releasing estra-1,3,5,16-tetraene analogs (NO-∆-16-CIEAs) was designed and synthesized as dual inhibitors for EGFR and MRP2 based on our previous findings on estra-1,3,5-triene analog NO-CIEA 17 against both HepG2 and HepG2-R cell lines. Among the target compounds, 14a (R-isomer) and 14b (S-isomer) displayed potent anti-proliferative activity against both HepG2 and HepG2-R

  基于我们之前对 estra-1 的研究结果，设计并合成了一系列新的释放一氧化氮的 estra-1,3,5,16-四烯类似物 (NO-Δ-16-CIEAs) 作为 EGFR 和 MRP2 的双重抑制剂， 3,5-三烯类似物 NO-CIEA 17 针对 HepG2 和 HepG2-R 细胞系。在目标化合物中，与参比药物厄洛替尼相比，14a（R-异构体）和 14b（S-异构体）对 HepG2 和 HepG2-R 细胞系均显示出有效的抗增殖活性。值得注意的是，化合物 14a 在浓度为 1.20 µM 时导致 EGFR 磷酸化显着降低，对 MEK1/2 和 ERK1/2 的磷酸化具有轻微活性。它还以剂量依赖性方式抑制 MRP2 表达，抑制率为 24%，并使细胞停滞在细胞周期的 S 期。有趣的是，与先导雌三烯类似物相比，化合物 14a（雌四烯核心）对 HepG2 和 HepG2-R 的抗增殖活性增加了两倍，证明了设计的