12alpha-Hydroxytriptolide | 883976-18-9

• 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: 12alpha-Hydroxytriptolide
• 英文别名: (1S,2S,4S,5R,8S,10S,12S)-5-hydroxy-1-methyl-6-propan-2-yl-3,9,15-trioxahexacyclo[10.7.0.02,4.02,8.08,10.013,17]nonadeca-6,13(17)-dien-16-one
• CAS: 883976-18-9
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: DFNSBQRVBFPSGQ-SQYQGHBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12alpha-Hydroxytriptolide 在 sodium hydroxide 、 sodium tetrahydroborate 、 双氧水 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (1S,2S,4S,5R,6R,8R,9R,11S,13S)-5-hydroxy-1-methyl-6-propan-2-yl-3,7,10,16-tetraoxaheptacyclo[11.7.0.02,4.02,9.06,8.09,11.014,18]icos-14(18)-en-17-one
  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：

  雷公藤甲素 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

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 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.