10β-benzoylmethyl-10-deoxoartemisin | 253774-86-6

• 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: 10β-benzoylmethyl-10-deoxoartemisin
• 英文别名: 10-(2-oxo-2-phenylethyl)deoxoartemisinin；1-phenyl-2-[(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]ethanone
• CAS: 253774-86-6
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: TYYWFMKZJVXBKU-DFIIIMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10β-benzoylmethyl-10-deoxoartemisin 在 BAST 作用下， 以22%的产率得到
  参考文献：
  名称：

  New chemical and biological aspects of artemisinin-Derived trioxane dimers

  摘要：

  Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. H-1 NMR spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dinners 5a and 5b, are promising for chemotherapy of both malaria and cancer. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00270-x
• 作为产物：
  描述：

  双氢青蒿素 在 吡啶 、 4-二甲氨基吡啶 、 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 10β-benzoylmethyl-10-deoxoartemisin
  参考文献：
  名称：

  10-取代的脱氧青蒿素的合成及其抗疟活性。

  摘要：

  已经合成了两个系列的10-取代的脱氧青蒿素衍生物。第一种方法是在四氯化钛存在下，使乙酸双氢青蒿素与几种甲硅烷基烯醇醚反应。第二种利用10-（2-氧代乙基）脱氧青蒿素与几种格氏试剂的反应。确定了两个系列对恶性疟原虫两个耐药克隆的体外抗疟活性。13 beta和15 beta的活性是青蒿素的5-7倍。

  DOI：

  10.1021/jm000195l

文献信息

• A new synthetic route to 10β-alkyldeoxoartemisinins
  作者：Jingyuan Ma、Esther Katz、Herman Ziffer

  DOI：10.1016/s0040-4039(99)01824-9

  日期：1999.12

  Artemisinin was reduced with DIBAL and acetylated to yield 10 alpha-acetoxyartemisinin. The latter compound was treated with titanium tetrachloride and a series of trimethylsiloxyl enol ethers to produce a series of 10 beta-alkyldeoxoartemisinins. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Syntheses and Antimalarial Activities of 10-Substituted Deoxoartemisinins
  作者：Jingyuan Ma、Esther Katz、Dennis E. Kyle、Herman Ziffer

  DOI：10.1021/jm000195l

  日期：2000.11.1

  Two series of 10-substituted deoxoartemisinin derivatives have been synthesized. The first employed the reaction of dihydroartemisinin acetate with several silyl enol ethers in the presence of titanium tetrachloride. The second utilized the reaction of 10-(2-oxoethyl)deoxoartemisinin with several Grignard reagents. The in vitro antimalarial activities of both series were determined against two drug-resistant

  已经合成了两个系列的10-取代的脱氧青蒿素衍生物。第一种方法是在四氯化钛存在下，使乙酸双氢青蒿素与几种甲硅烷基烯醇醚反应。第二种利用10-（2-氧代乙基）脱氧青蒿素与几种格氏试剂的反应。确定了两个系列对恶性疟原虫两个耐药克隆的体外抗疟活性。13 beta和15 beta的活性是青蒿素的5-7倍。
• New chemical and biological aspects of artemisinin-Derived trioxane dimers
  作者：Gary H Posner、John Northrop、Ik-Hyeon Paik、Kristina Borstnik、Patrick Dolan、Thomas W Kensler、Suji Xie、Theresa A Shapiro

  DOI：10.1016/s0968-0896(01)00270-x

  日期：2002.1

  Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. H-1 NMR spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dinners 5a and 5b, are promising for chemotherapy of both malaria and cancer. (C) 2001 Elsevier Science Ltd. All rights reserved.