ethyl ent-15α-hydroxymethyl-16β-isothiocyanobeyeran-19-oate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl ent-15α-hydroxymethyl-16β-isothiocyanobeyeran-19-oate
• 英文别名: ethyl (1S,4S,5R,9S,10S,13S,14R,15S)-15-(hydroxymethyl)-14-isothiocyanato-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• 化学式: C₂₄H₃₇NO₃S
• 分子量: 419.629
• InChiKey: CPEWTGNCLJCRQR-QLSAUNAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  异甜菊醇 在 sodium tetrahydroborate 、 乙醇 、 盐酸羟胺 、 sodium 、 碳酸氢钠 、 三乙胺 、 molybdenum(VI) oxide 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 22.5h， 生成 ethyl ent-15α-hydroxymethyl-16β-isothiocyanobeyeran-19-oate
  参考文献：
  名称：

  Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents

  摘要：

  A series of novel isosteviol derivatives bearing amino alcohol and thiourea fragments have been stereo selectively synthesized and screened for their in vitro cytotoxic activities against three human cancer cell lines (HCT-116, HGC-27 and JEKO-1). The results demonstrated that these compounds exhibited prominent cytotoxicities. Especially, the compound Iw displayed the most potent anticancer activities against HCT-116 cell with IC50 value of 1.450 mu M. On the basis of this bioassay results, these derivatives were further investigated by the hologram quantitative structure activity relationship (HQSAR) technique. The optimal HQSAR model with q(2) = 0.663, r(2) = 0.895, SEE = 0.179 was generated using A/B/H/Ch as fragment distinction parameters and 4-7 as fragment size. This model was employed to predict the cytotoxic activities of test set compounds, and the predicted values were in good agreement with the experimental results. The contribution maps derived from the optimal model explained the individual atomic contribution to the total activity of single molecule. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.009