(4S,20S,22R)-27-acetoxy-4-(p-bromobenzoyloxy)-1-oxo-witha-2,5,16,24-tetraenolide | 1251712-71-6

• 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: (4S,20S,22R)-27-acetoxy-4-(p-bromobenzoyloxy)-1-oxo-witha-2,5,16,24-tetraenolide
• 英文别名: [(4S,8S,9S,10R,13S,14S)-17-[(1S)-1-[(2R)-5-(acetyloxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-4-yl] 4-bromobenzoate
• CAS: 1251712-71-6
• 化学式: C₃₇H₄₁BrO₇
• 分子量: 677.632
• InChiKey: WQCIECRDLVHDDM-CJKNZDMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4S,20S,22R)-27-acetoxy-4-hydroxy-1-oxo-witha-2,5,16,24-tetraenolide 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以2.2 mg的产率得到(4S,20S,22R)-27-acetoxy-4-(p-bromobenzoyloxy)-1-oxo-witha-2,5,16,24-tetraenolide
  参考文献：
  名称：

  Withanolides from Withania aristata and their cytotoxic activity

  摘要：

  Seven new withanolides (1-7), along with three known ones (8-10), were isolated from the leaves of Withania aristata. Their structures were elucidated on the basis of spectroscopic analysis, including 2D NMR experiments and spectrometric techniques, and the absolute configuration of 1 and 2 was established by CD analysis. In the search for new cytotoxic compounds from Withania species, the isolated compounds 1-9, along with two derivatives, were assayed for their cytotoxicity against HeLa, MCF-7 and A-549 human tumor cell lines. Derivative (4S,20R,22R)-27-acetoxy-4-p-bromobenzoyloxy-1-oxo-witha-2,5,16,24-tetraenolide (13) showed cytotoxicity against all the cell lines assayed with IC(50) values ranging from 2.8 to 3.6 mu M, and (4S,20R,22R)-4,27-diacetoxy-4-hydroxy-1-oxo-witha-2,5,16,24-tetraenolide (12) exhibited an IC(50) value of 5.4 mu M on the MCF-7 cell line. (C) 2010 Elsevier Inc. All rights reserved,

  DOI：

  10.1016/j.steroids.2010.06.001