ethyl ent-16β-aminobeyeran-19-oate | 1352335-14-8

• 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-16β-aminobeyeran-19-oate
• 英文别名: ethyl 16α-aminobeyeran-19-oate；ethyl (1R,4S,5R,9S,10R,13S,14R)-14-amino-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1352335-14-8
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: LUSCIWPNMAKTHY-QIVLDXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl ent-16β-aminobeyeran-19-oate 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 ethyl ent-16β-cyclohexylcarbamothioylaminobeyeran-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
• 作为产物：
  描述：

  异甜菊醇 在 sodium tetrahydroborate 、 盐酸羟胺 、 碳酸氢钠 、 molybdenum(VI) oxide 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 ethyl ent-16β-aminobeyeran-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

文献信息

• Chiral Primary Amine–Squaramide Catalyzed Highly Enantio­selective Michael Addition of Isobutyraldehyde to Nitroolefins
  作者：Zhi-Wei Ma、Jing-Chao Tao、Xiao-Feng Liu、Bin Sun、Xian-Hui Huang

  DOI：10.1055/s-0036-1588090

  日期：——

  to 98%) with high to excellent enantioselectivities (up to 99% ee). Chiral primary amine–squaramides have not been extensively studied to date in the field of organocatalysis. In this paper, novel chiral squaramides derived from natural product stevioside were developed. Both enantiomers of a series of γ-nitroaldehydes were generated by using these squaramide catalysts for the Michael addition reaction

  摘要 迄今为止，手性伯胺-方酰胺在有机催化领域尚未得到广泛研究。本文开发了一种从天然产物甜菊糖苷衍生的新型手性方酸酰胺。通过使用这些方形酰胺催化剂将异丁醛与硝基烯烃进行迈克尔加成反应，可以生成一系列γ-硝基醛的两种对映异构体。该不对称反应进行得很好，以高产率（高达98％）和高至优异的对映选择性（高达99％ee）提供了所需的产物。 迄今为止，手性伯胺-方酰胺在有机催化领域尚未得到广泛研究。本文开发了一种从天然产物甜菊糖苷衍生的新型手性方酸酰胺。通过使用这些方形酰胺催化剂将异丁醛与硝基烯烃进行迈克尔加成反应，可以生成一系列γ-硝基醛的两种对映异构体。该不对称反应进行得很好，以高产率（高达98％）和高至优异的对映选择性（高达99％ee）提供了所需的产物。
• 一种16-氨基异斯特维醇乙酯非对映异构体混 合物的分离方法
  申请人：河南工程学院

  公开号：CN105503629B

  公开（公告）日：2017-07-14

  本发明属于医药化工中间体非对映异构体的分离技术领域，具体公开了一种16‑氨基异斯特维醇乙酯非对映异构体混合物的分离方法。将16‑氨基异斯特维醇乙酯非对映异构体混合物用乙醇溶解，在冰浴条件下向体系中滴加0.5摩尔当量的邻硝基苯甲酸的乙醇溶液，滴加完毕后，浓缩反应体系，用乙酸乙酯结晶，过滤，滤饼为其中一种构型的16‑氨基异斯特维醇乙酯异构体的盐类，该盐再加碱液中和处理除酸，即获得其中一种构型的16‑氨基异斯特维醇乙酯异构体，而滤液则再经柱层析分离，得到另外一种构型的16‑氨基异斯特维醇乙酯异构体。本发明分离方法操作简便，分离彻底。
• A highly efficient large-scale asymmetric Michael addition of isobutyraldehyde to maleimides promoted by a novel multifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Pan-li Li、Hang Ren、Yu Zhu、Jing-chao Tao

  DOI：10.1016/j.tetasy.2011.10.002

  日期：2011.10

  A novel class of chiral multifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a primary amino group were designed and prepared. The thioureas were proven to be effective for catalyzing the asymmetric Michael addition between isobutyraldehyde and maleimides with only 0.5 mol% catalyst loading, and exhibited double asymmetric induction. Both of the catalysts afforded the corresponding adduct with high to excellent yields (up to 98%) and excellent enantioselectivities (up to 99%). Furthermore, this catalytic system can be used efficiently in large-scale reactions with the yields and enantioselectivities being maintained at the same level. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis, cytotoxic activity evaluation and HQSAR study of novel isosteviol derivatives as potential anticancer agents
  作者：Cong-Jun Liu、Shu-Ling Yu、Yan-Ping Liu、Xing-Jie Dai、Ya Wu、Rui-Jun Li、Jing-Chao Tao

  DOI：10.1016/j.ejmech.2016.03.009

  日期：2016.6

  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.