(3S)-3-hydroxy-2-methylidene-4-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]butanenitrile | 1315563-05-3

• 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: (3S)-3-hydroxy-2-methylidene-4-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]butanenitrile
• CAS: 1315563-05-3
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: RZGGXGIICUEADL-OILSFMFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  10-deoxoallylartemisinin 在 三乙烯二胺 、 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (3S)-3-hydroxy-2-methylidene-4-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]butanenitrile 、 (3R)-3-hydroxy-2-methylidene-4-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]butanenitrile
  参考文献：
  名称：

  NEW SERIES OF ARTEMISININ DERIVATIVES AND PROCESS FOR PREPARATION THEREOF

  摘要：

  这项发明涉及合成某些新颖的Baylis-Hillman加合物，其来源于青蒿素衍生醛2[10′β-去氧青蒿素基]-乙醛。利用Baylis-Hillman反应一步引入分子中三个功能团的能力鼓励我们合成一些高度官能化的青蒿素衍生物。本文所述的这些高度官能化的青蒿素衍生物被发现对各种癌细胞系具有活性。

  公开号：

  US20130030044A1

文献信息

• [EN] A NEW SERIES OF ARTEMISININ DERIVATIVES AND PROCESS FOR PREPARATION THEREOF<br/>[FR] NOUVELLE SÉRIE DE DÉRIVÉS D'ARTÉMISININE ET SON PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2011089507A1

  公开（公告）日：2011-07-28

  This invention relates to the synthesis of certain novel Baylis-Hillman adducts of artremisinin derived aldehyde 2-[10'β-deoxoartemisininyl]-ethanal. The capabilities of introduction of three functional groups into a molecule in one step using Baylis-Hillman reaction encouraged us to synthesize some highly functionalized derivatives of artemisinin. These highly functionalized artemisinin derivatives embodied in this document are found to be active against various cancer cell-lines

  这项发明涉及合成某些新颖的Baylis-Hillman加合物，其源自青蒿素衍生醛2-[10'β-去氧青蒿素基]-乙醛。利用Baylis-Hillman反应一步引入分子中三个官能团的能力鼓励我们合成一些高度官能化的青蒿素衍生物。本文件中包含的这些高度官能化的青蒿素衍生物被发现对各种癌细胞系具有活性。
• Synthesis of a novel series of highly functionalized Baylis–Hillman adducts of artemisinin with potent anticancer activity
  作者：Abhishek Goswami、Partha P. Saikia、Bishwajit Saikia、Nabin C. Barua、Ajit K. Saxena、Nitasha Suri、Madhunika Sharma、Gakul Baishya

  DOI：10.1016/j.tetlet.2013.05.123

  日期：2013.8

  A novel series of densely functionalized derivatives of artemisinin have been synthesized using Baylis-Hillman reaction and their further applicability has been demonstrated. The in vitro anticancer activity of these adducts against a panel of human cancer cell lines is summarized. Compound 10 (% GI of 100 against colon colo-205; % GI of 85 against Lung A-549), 7b (% GI of 78 against prostrate PC-3) and 9a, 9b (% GI of 71 against prostrate PC-3) were especially potent in inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. These newly synthesized compounds can be further utilized as potential precursor for the synthesis of libraries of new artemisinin analogs including dimer. (C) 2013 Elsevier Ltd. All rights reserved.