[(2R)-4-[2-[(1S)-1-[(3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-1,3-dioxolan-2-yl]-2-methylbutyl] 2,2-dimethylpropanoate | 1375576-52-5

• 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: [(2R)-4-[2-[(1S)-1-[(3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-1,3-dioxolan-2-yl]-2-methylbutyl] 2,2-dimethylpropanoate
• CAS: 1375576-52-5
• 化学式: C₄₀H₇₀O₅Si
• 分子量: 659.078
• InChiKey: YOMYTBNIABOOMK-CMNMLBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.34
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2R)-4-[2-[(1S)-1-[(3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-1,3-dioxolan-2-yl]-2-methylbutyl] 2,2-dimethylpropanoate 在 吡啶 、 四氧化锇 、 草酰氯 、 二甲基亚砜 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S,17S)-3,17-dihydroxy-10,13-dimethyl-16-oxo-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-5-oxoheptyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis and antitumor activity of 5,6-dihydro-17-hydroxy icogenin analogs

  摘要：

  Four 5,6-dihydro-17-hydroxy icogenin analogs were designed and synthesized. Their in vitro antitumor activities were tested by the standard MTT assay. Compound 22 (IC50 = 3.38-8.30 mu M) and compound 23 (IC50 = 1.90-9.69 mu M) showed potential antitumor activities against the entire tested seven cancer cell lines. The SAR (structure activity relationship) research showed that the introduction of 17-hydroxy lowered the antitumor activity to an extent. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.043
• 作为产物：
  描述：

  在 咪唑 、 4-二甲氨基吡啶 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 [(2R)-4-[2-[(1S)-1-[(3S,5S,8R,9S,10S,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-1,3-dioxolan-2-yl]-2-methylbutyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis and antitumor activity of 5,6-dihydro-17-hydroxy icogenin analogs

  摘要：

  Four 5,6-dihydro-17-hydroxy icogenin analogs were designed and synthesized. Their in vitro antitumor activities were tested by the standard MTT assay. Compound 22 (IC50 = 3.38-8.30 mu M) and compound 23 (IC50 = 1.90-9.69 mu M) showed potential antitumor activities against the entire tested seven cancer cell lines. The SAR (structure activity relationship) research showed that the introduction of 17-hydroxy lowered the antitumor activity to an extent. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.043

文献信息

• Synthesis and antitumor activity of 5,6-dihydro-17-hydroxy icogenin analogs
  作者：Yu-yao Guan、Dan Zheng、Zheng Yan、Nan Wang、Ping-sheng Lei

  DOI：10.1016/j.ejmech.2012.02.043

  日期：2012.5

  Four 5,6-dihydro-17-hydroxy icogenin analogs were designed and synthesized. Their in vitro antitumor activities were tested by the standard MTT assay. Compound 22 (IC50 = 3.38-8.30 mu M) and compound 23 (IC50 = 1.90-9.69 mu M) showed potential antitumor activities against the entire tested seven cancer cell lines. The SAR (structure activity relationship) research showed that the introduction of 17-hydroxy lowered the antitumor activity to an extent. (C) 2012 Elsevier Masson SAS. All rights reserved.