(1S,2S,4S,5S,7S,8R,9S,11S,13S)-8-fluoro-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one | 753020-26-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,2S,4S,5S,7S,8R,9S,11S,13S)-8-fluoro-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,7.09,11.014,18]icos-14(18)-en-17-one
• CAS: 753020-26-7
• 化学式: C₂₀H₂₃FO₅
• 分子量: 362.398
• InChiKey: YQVRBZDSASHMKI-CIVMWXNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  14-epitriptolide 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以35%的产率得到(1S,2S,4S,5R,7R,8S,9S,11S,13S)-7-fluoro-1-methyl-7-propan-2-yl-3,6,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.05,8.09,11.014,18]icos-14(18)-en-17-one
  参考文献：
  名称：

  雷公藤甲素及其类似物的氟化及其细胞毒性。

  摘要：

  研究了雷公藤甲素及其类似物与氟化剂，即双（2-甲氧基乙基）氨基三氟化硫（Deoxo-Fluor）或（二乙基氨基）三氟化硫（DAST）的反应。发现一种氟化产物14β-去羟基-14β-氟雷公藤内酯醇比母体天然雷公藤内酯醇更具细胞毒性。

  DOI：

  10.1016/j.bmcl.2008.02.039

文献信息

• TRIPTOLIDE DERIVATIVES AND PREPARATION METHOD AND USE THEREOF
  申请人：Hong Kong Baptist University

  公开号：US20160362691A1

  公开（公告）日：2016-12-15

  Tripyolide-nucleic acid aptamer derivatives, a preparation method and use thereof are shown. The structure of the triptolide-nucleic acid aptamer derivatives is as shown by formula I, wherein the definitions of R 1 -R 7 , G, A, B, M, Z and X are described. The present invention uses a nucleic acid aptamer and triptolide or modified compounds thereof as the starting materials, and introduces a linking group A at the C-14 hydroxyl group, epoxy groups and five-membered ring lactones in triptolide, then connects it to a nucleic acid aptamer B, and obtains the triptolide-nucleic acid aptamer derivatives. The triptolide-nucleic acid aptamer derivatives of the present invention have the characteristics of good targeting, a high anti-cancer activity, low toxicity and side effects, good water solubility and high bioavailability, and the preparation method of the present invention is scientific and reasonable and has a controllable quality and good repeatability, and is thereby suitable for production.
• US9809822B2
  申请人：——

  公开号：US9809822B2

  公开（公告）日：2017-11-07
• Fluorination of triptolide and its analogues and their cytotoxicity
  作者：Yutaka Aoyagi、Yukio Hitotsuyanagi、Tomoyo Hasuda、Saki Matsuyama、Haruhiko Fukaya、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto

  DOI：10.1016/j.bmcl.2008.02.039

  日期：2008.4

  The reaction of triptolide and its analogues with a fluorinating agent, that is, bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor) or (diethylamino)sulfur trifluoride (DAST), was studied. One of the fluorinated products, 14beta-dehydroxy-14beta-fluoro triptolide, was found to be more cytotoxic than the parent natural triptolide.

  研究了雷公藤甲素及其类似物与氟化剂，即双（2-甲氧基乙基）氨基三氟化硫（Deoxo-Fluor）或（二乙基氨基）三氟化硫（DAST）的反应。发现一种氟化产物14β-去羟基-14β-氟雷公藤内酯醇比母体天然雷公藤内酯醇更具细胞毒性。