14-epitriptolide | 144539-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 14-epitriptolide
• 英文别名: epi-triptonide；epitriptolide；14-Epi-triptolide；(1S,2S,4S,5S,7R,8S,9S,11S,13S)-8-hydroxy-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: 144539-79-7
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: DFBIRQPKNDILPW-FKXGARDLSA-N

物化性质

• 沸点：
  601.7±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  84.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  14-epitriptolide 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 12alpha-Hydroxytriptolide
  参考文献：
  名称：

  Semisynthesis of C-ring modified triptolide analogues and their cytotoxic activities

  摘要：

  Several C-ring modified analogues of a potent antileukemic diterpene, triptolide (1), were synthesized and their structure-activity relationships were studied. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.098
• 作为产物：
  描述：

  雷公藤内酯酮 在 sodium tetrahydroborate 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以49%的产率得到14-epitriptolide
  参考文献：
  名称：

  有效合成关键的中间体雷公藤酚甲醚用于合成（-）-雷公藤内酯

  摘要：

  从九个步骤中容易获得的松香酸3高效合成了雷公藤多酚甲醚4，并已成功应用于（-）-雷公藤内酯1的合成。该路线具有成本低，产量高，易于操作的特点。此外，此路线中的每个反应均已成功扩大规模至100 g底物水平，而没有损失收率。

  DOI：

  10.1016/j.tet.2010.05.035

文献信息

• 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。
• Semisynthesis of triptolide analogues: Effect of γ-lactone and C-14 substituents on cytotoxic activities
  作者：Yutaka Aoyagi、Yukio Hitotsuyanagi、Tomoyo Hasuda、Haruhiko Fukaya、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto

  DOI：10.1016/j.bmcl.2011.03.025

  日期：2011.5

  Triptolide gamma-lactone and C-14 analogues were prepared and evaluated cytotoxity against human lung adenocarcinoma epithelial A549 cells and human colon adenocarcinoma HT-29 cells. gamma-Lactone substructure and C-14 substituents affected the biological activities significantly. (C) 2011 Elsevier Ltd. All rights reserved.
• Efficient synthesis of the key intermediate triptophenolide methyl ether for the synthesis of (−)-triptolide
  作者：Bing Zhou、Xiaomei Li、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.tet.2010.05.035

  日期：2010.7

  An efficient synthesis of triptophenolide methyl ether 4 from the readily available abietic acid 3 in nine steps is described and successfully applied to the synthesis of (−)-triptolide 1. The route is of characteristic of low cost, high yield and easy operation. In addition, every reaction in this route has been successfully scaled-up to a 100 g substrate level without loss of yield.

  从九个步骤中容易获得的松香酸3高效合成了雷公藤多酚甲醚4，并已成功应用于（-）-雷公藤内酯1的合成。该路线具有成本低，产量高，易于操作的特点。此外，此路线中的每个反应均已成功扩大规模至100 g底物水平，而没有损失收率。
• Semisynthesis of C-ring modified triptolide analogues and their cytotoxic activities
  作者：Yutaka Aoyagi、Yukio Hitotsuyanagi、Tomoyo Hasuda、Haruhiko Fukaya、Koichi Takeya、Ritsuo Aiyama、Takeshi Matsuzaki、Shusuke Hashimoto

  DOI：10.1016/j.bmcl.2005.12.098

  日期：2006.4

  Several C-ring modified analogues of a potent antileukemic diterpene, triptolide (1), were synthesized and their structure-activity relationships were studied. (C) 2006 Elsevier Ltd. All rights reserved.