ethyl (16α)-16-[(prop-2-enoyl)oxy]beyeran-18-oate | 1143505-93-4

• 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 (16α)-16-[(prop-2-enoyl)oxy]beyeran-18-oate
• 英文别名: ethyl ent-16-α-acryloyloxybeyeran-19-oate；ethyl ent-16β-acryloxybeyeran-19-oate；ethyl (1R,4S,5R,9S,10R,13S,14R)-5,9,13-trimethyl-14-prop-2-enoyloxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 1143505-93-4
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: JSPWDSUJISYNSY-DBWGLHGNSA-N

物化性质

• 沸点：
  461.8±38.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异甜菊醇 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 13.0h， 生成 ethyl (16α)-16-[(prop-2-enoyl)oxy]beyeran-18-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

• 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.
• Stereoselective synthesis of 15- and 16-substituted isosteviol derivatives and their cytotoxic activities
  作者：Ya Wu、Gui-Fu Dai、Jing-Hua Yang、Yun-Xiao Zhang、Yu Zhu、Jing-Chao Tao

  DOI：10.1016/j.bmcl.2008.12.101

  日期：2009.3

  By means of functional interconversions in ring D of the tetracyclic diterpene isosteviol (ent-16-ketobeyeran-19-oic acid 1), various 15- and 16-substituted isosteviol derivatives were stereoselectively prepared. The cytotoxic activities in vitro of these new isosteviol derivatives were investigated, and some of them showed noteworthy activities against B16-F10 melanoma cells. (C) 2009 Published by Elsevier Ltd.