ethyl ent-16β-isothiocyanobeyeran-19-oate | 1352335-15-9

• 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-isothiocyanobeyeran-19-oate
• 英文别名: ethyl 16α-isothiocyanatobeyeran-19-oate；ethyl (1R,4S,5R,9S,10R,13S,14R)-14-isothiocyanato-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1352335-15-9
• 化学式: C₂₃H₃₅NO₂S
• 分子量: 389.602
• InChiKey: RGYPPLKKXAKBRV-KIEPGZPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl ent-16β-isothiocyanobeyeran-19-oate 、 (S)-(-)- α-甲基苄胺 以 二氯甲烷 为溶剂， 以82%的产率得到ethyl ent-16β-((S)-1'-phenylethyl)carbamothioylaminobeyeran-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 、 三乙胺 、 molybdenum(VI) oxide 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 ethyl ent-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

文献信息

• Doubly stereocontrolled asymmetric Michael addition of acetylacetone to nitroolefins promoted by an isosteviol-derived bifunctional thiourea
  作者：Zhi-wei Ma、Yu-xia Liu、Li-juan Huo、Xiang Gao、Jing-chao Tao

  DOI：10.1016/j.tetasy.2012.03.020

  日期：2012.4

  A novel class of chiral bifunctional thioureas bearing a chiral lipophilic beyerane scaffold and a tertiary amino group was designed and prepared. The thioureas were proven to be effective for catalyzing the doubly stereocontrolled asymmetric Michael addition between acetylacetone and nitroolefins. The corresponding adducts were obtained in high yields (up to 95%) and with good to excellent enantioselectivities

  设计并制备了一类新型的手性双官能硫脲，该手性双官能硫脲带有手性亲脂性拜亚烷骨架和叔氨基。硫脲被证明可有效催化乙酰丙酮和硝基烯烃之间的双立体控制的不对称迈克尔加成反应。相应的加合物以高收率（最高95％）和良好至优异的对映选择性（最高97％）获得。此外，乙酰乙酸叔丁酯与反式-β-硝基苯乙烯的反应也顺利进行，具有良好的对映选择性。
• Enantioselective Michael Addition of Pyrazolin-5-ones to Nitroalkenes Catalyzed by Novel Squaramide Organocatalyst
  作者：Zhi-Wei Ma、Quan-Jian Lv、Xiao-Feng Liu、Xiao-Pei Chen、Chuan-Chuan Wang、Jing-Chao Tao

  DOI：10.2174/1570178619666220128142038

  日期：2022.10

  A new tertiary amine-thiourea organocatalyst has successfully been developed and applied into the asymmetric Michael addition of pyrazolin-5-one to nitroalkenes. The catalyst system performed well with a low catalyst loading of 5 mol% under mild reaction conditions. A series of synthetically and pharmaceutically useful chiral pyrazolone derivatives was obtained in high yields (up to 95%) with good enantioselectivities (up to 88 % ee).

  摘要： 成功开发了一种新的叔胺-硫脲有机催化剂，并将其应用于吡唑啉-5-酮与硝基烯烃的不对称迈克尔加成反应。 将其成功应用于吡唑啉-5-酮与硝基烯烃的不对称迈克尔加成反应。催化剂体系 在温和的反应条件下，催化剂负载量较低，仅为 5 mol%。一系列 获得了一系列在合成和制药上有用的手性吡唑啉酮衍生物，产率高（达 95%），且具有良好的催化活性。 (高达 95%）和良好的对映选择性（高达 88 % ee）。
• 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.