ethyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate | 882175-41-9

• 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-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate
• 英文别名: ethyl ent-16β-hydroxy-15α-hydroxymethylbeyeran-19-oate；ethyl (15β,16α)-16-hydroxy-15-(hydroxymethyl)beyeran-18-oate；ethyl (1S,4S,5R,9S,10S,13S,14R,15R)-14-hydroxy-15-(hydroxymethyl)-5,9,13-trimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 882175-41-9
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: MRZQIURTRURFJR-FDSZRRAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 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 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到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
• 作为产物：
  描述：

  异甜菊醇 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 ethyl ent-15α-hydroxymethyl-16β-hydroxybeyeran-19-oate
  参考文献：
  名称：

  D环修饰的新型异戊烯醇衍生物：设计，合成和细胞毒性活性评估

  摘要：

  通过异戊烯醇的D环修饰，可以轻松合成一系列多元醇，氨基醇和三环衍生物。筛选了这些化合物在体外对四种人类肿瘤细胞系的细胞毒活性。其中，15-α-氨基甲基-16-β-羟基异黄酮醇23对EC9706，PC-3和HCT-116细胞系表现出明显优于阳性对照（顺铂）的细胞毒性。

  DOI：

  10.1016/j.bmcl.2012.07.083

文献信息

• Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents
  作者：Song-Lin Zhu、Ya Wu、Cong-Jun Liu、Chang-Yong Wei、Jing-Chao Tao、Hong-Min Liu

  DOI：10.1016/j.ejmech.2013.04.044

  日期：2013.7

  Two series of novel isosteviol-fused pyrazoline and pyrazole derivatives were facilely synthesized via intramolecular 1,3-dipolar cycloaddition and condensation reaction, respectively. All compounds were characterized by NMR, IR and HRMS spectra. The stereochemistry of compounds 9b, 10, 11a and 11v were further confirmed by X-ray crystallographic analysis. The antiproliferative activities of the structurally

  分别通过分子内的1,3-偶极环加成和缩合反应轻松合成了两个新的异戊烯醇稠合的吡唑啉和吡唑衍生物。所有化合物均通过NMR，IR和HRMS光谱进行表征。化合物的立体化学9b的，10，11A和11V用X射线结晶学分析进一步证实。在体外测试了与结构相关的吡唑啉和吡唑衍生物的抗增殖活性在四种人类恶性细胞系（SGC 7901，A549，Raji和HeLa）上：我们的结果表明，异戊四醇融合的吡唑衍生物表现出值得注意的细胞毒活性。其中，与顺铂相比，针对SGC 7901，A549，Raji和HeLa的2,4-二-Cl-苯基吡唑衍生物11t表现出更好的细胞毒性，IC 50值分别为2.71、3.18、1.09和13.52μM，IC50值与顺铂相比（IC 50值：分别为7.56、17.78、17.32和14.31μM）。
• 含有ent-贝叶烷骨架的手性冠醚及其制备方 法和应用
  申请人：浙江工业大学

  公开号：CN105566283B

  公开（公告）日：2017-12-05

  本发明提供了式(I)或式(II)所示的含有ent‑贝叶烷骨架的手性冠醚及其制备方法，该手性冠醚作为受体在识别手性分子客体方面具有一定的应用前景，其中所述的手性分子客体包括手性氨类化合物及手性羟基化合物，具体例如：D/L‑苯甘氨酸甲酯盐酸盐或D/L‑苯甘氨酸乙酯盐酸盐；本发明所提供的以ent‑贝叶烷结构为手性源的手性冠醚化合物具有原料易得、结构可调整、制备简洁等优点，可以在手性分子识别体系中作为受体，有望在手性识别分离领域得到应用。
• Syntheses, cytotoxic activity evaluation and HQSAR study of 1,2,3-triazole-linked isosteviol derivatives as potential anticancer agents
  作者：Cong-Jun Liu、Yan-Ping Liu、Shu-Ling Yu、Xing-Jie Dai、Tao Zhang、Jing-Chao Tao

  DOI：10.1016/j.bmcl.2016.10.028

  日期：2016.11

  A series of novel 1,2,3-triazole-linked isosteviol derivatives were designed and synthesized via Huisgen-click reaction. Their cytotoxicities in vitro against HCT-116 and JEKO-1 cells were screened. The preliminary bioassays indicated that most of the title compounds exhibited noteworthy cytotoxic activities. Particularly, the compound 10b revealed the most potent inhibitory activities against HCT-116

  通过Huisgen-click反应设计并合成了一系列新颖的1,2,3-三唑连接的异戊烯醇衍生物。筛选了它们对HCT-116和JEKO-1细胞的体外细胞毒性。初步的生物测定表明，大多数标题化合物表现出值得注意的细胞毒活性。特别地，化合物10b显示出对HCT-116细胞最有效的抑制活性，IC50值为2.987±0.098μM，优于阳性对照顺铂的（3.906±0.261μM）。基于这些生物活性数据，进行了全息图定量结构-活性关系（HQSAR），并获得了具有良好预测能力（r2 = 0.848，q2 = 0.544和R2pred = 0.982）的统计可靠模型。此外，
• 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.