ethyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate | 1143505-95-6

• 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-hydroxybeyeran-19-oate
• 英文别名: ethyl ent-15α-hydroxymethyl-16-oxobeyeran-19-oate；ethyl (15β)-15-(hydroxymethyl)-16-oxobeyeran-18-oate；ethyl (1S,4S,5R,9S,10S,13S,15R)-15-(hydroxymethyl)-5,9,13-trimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1143505-95-6
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: NCBNKUDLJLORAA-UQRNBJPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate 在 sodium tetrahydroborate 、 盐酸羟胺 、 碳酸氢钠 、 molybdenum(VI) oxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 ethyl ent-15α-hydroxymethyl-16β-(2'-nitrophenyl)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 ethanolate 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 ethyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate
  参考文献：
  名称：

  具有D环修饰的新型异osteviol衍生物的立体选择性合成，表征和抗菌活性

  摘要：

  异osteviol及其衍生物因其多种生物活性而引起了极大的兴趣。在该项目中，通过四环二萜异戊二烯醇D环中的功能性相互转化，立体选择性地制备了一系列新型的15和16取代的异雌甾醇。通过NMR，IR，HR-MS数据分析对所有合成的化合物进行表征，并通过X射线晶体学分析确定33和37的构型。研究了这些异osteviol衍生物的体外抗菌活性。该合成的化合物针对更活跃的革兰氏阳性比革兰氏阴性细菌，对枯草芽孢杆菌特别活跃。其中，化合物27（MIC = 1.56μg/ ml）表现出最高的抗菌活性，因此可以用作开发有效抗菌剂的先导化合物。

  DOI：

  10.1002/hlca.201000046

文献信息

• Synthesis, Structure, and Cytotoxic Activities of a Novel Lactam of the Diterpenoid Isosteviol
  作者：Cong-Jun Liu、Jing-Jing Li、Yu-Tao Min、Ling-Li Zhang、Bao-Yu Wang、Ya-Hao Wang

  DOI：10.1007/s10600-020-03171-3

  日期：2020.9

  A novel compound lactam of 15β-hydroxymethylisosteviol ethyl ester 3 has been synthesized and structurally characterized by IR, NMR, and HR-MS. Its X-ray crystallographic analysis revealed that the nitrogen is attached to C-13 instead of C-15. The reaction mechanism was discussed, and the title compound was further evaluated against HCT-116, HGC-27, and JEKO-1 cells by the MTT assay. The results demonstrated

  合成了 15β-羟甲基异甜菊醇乙酯 3 的新型复合内酰胺，并通过红外、核磁共振和 HR-MS 对其进行了结构表征。它的 X 射线晶体学分析表明，氮附着在 C-13 上而不是 C-15 上。讨论了反应机理，并通过 MTT 测定进一步评估了标题化合物对 HCT-116、HGC-27 和 JEKO-1 细胞的影响。结果表明，化合物3比其相应的前体异甜菊醇表现出更好的细胞毒活性。
• Stereoselective synthesis of bioactive isosteviol derivatives as α-glucosidase inhibitors
  作者：Ya Wu、Jing-Hua Yang、Gui-Fu Dai、Cong-Jun Liu、Guo-Qiang Tian、Wen-Yan Ma、Jing-Chao Tao

  DOI：10.1016/j.bmc.2009.01.017

  日期：2009.2

  Considerable interest has been attracted in isosteviol and its derivatives because of their large variety of pharmacological activities. In this project, a series of novel compounds containing hydroxyl, hydroxymethyl group and heteroatom-containing frameworks fused with isosteviol structure were synthesized and evaluated as alpha-glucosidase inhibitors, aimed at clarifying the structure-activity correlation. The results indicated that these isosteviol derivatives were capable of inhibiting in vitro alpha-glucosidase with moderate to good activities. Among them, indole derivative 15b exhibited the highest activities and thus may be exploitable as a lead compound for the development of potent alpha-glucosidase inhibitors. (c) 2009 Published by Elsevier Ltd.
• 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.
• Stereoselective Synthesis, Characterization, and Antibacterial Activities of Novel Isosteviol Derivatives with D-Ring Modification
  作者：Ya Wu、Cong-Jun Liu、Xu Liu、Gui-Fu Dai、Jin-Yu Du、Jing-Chao Tao

  DOI：10.1002/hlca.201000046

  日期：2010.10

  Considerable interests have been attracted by isosteviol and its derivatives because of their large variety of bioactivities. In this project, a series of novel 15‐ and 16‐substituted isosteviol derivatives were stereoselectively prepared by means of functional interconversions in ring D of the tetracyclic diterpene isosteviol. All compounds synthesized were characterized by analysis of NMR, IR, HR‐MS

  异osteviol及其衍生物因其多种生物活性而引起了极大的兴趣。在该项目中，通过四环二萜异戊二烯醇D环中的功能性相互转化，立体选择性地制备了一系列新型的15和16取代的异雌甾醇。通过NMR，IR，HR-MS数据分析对所有合成的化合物进行表征，并通过X射线晶体学分析确定33和37的构型。研究了这些异osteviol衍生物的体外抗菌活性。该合成的化合物针对更活跃的革兰氏阳性比革兰氏阴性细菌，对枯草芽孢杆菌特别活跃。其中，化合物27（MIC = 1.56μg/ ml）表现出最高的抗菌活性，因此可以用作开发有效抗菌剂的先导化合物。