10-(2-oxoethyl)deoxoartemisinin | 169174-16-7

• 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: 10-(2-oxoethyl)deoxoartemisinin
• 英文别名: 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]acetaldehyde
• CAS: 169174-16-7
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: HOHHKZXEBTWDGW-LTLPSTFDSA-N

物化性质

• 沸点：
  397.4±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  10-(2-oxoethyl)deoxoartemisinin 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以53%的产率得到12β-17,17-difluoroethyldeoxoartemisinin
  参考文献：
  名称：

  几种氟化青蒿素衍生物的合成和抗疟活性。

  摘要：

  几种青蒿素衍生物中的羰基在用二乙氨基三氟化硫处理后转化为孪生二氟化化合物。制备了许多其他单氟和多氟青蒿素衍生物。它们的体外抗疟活性均等于或大于非氟化类似物或前体。

  DOI：

  10.1021/jm00020a028
• 作为产物：
  描述：

  methyl artemisinate 在 sodium tetrahydroborate 、 二异丁基氢化铝 、 臭氧 、 magnesium 、 nickel dichloride 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 10-(2-oxoethyl)deoxoartemisinin
  参考文献：
  名称：

  An Efficient Synthesis of New Analogs of Water-soluble and Hydrolytically Stable Deoxoartemisinin

  摘要：

  Water-soluble and hydrolytically stable novel analogs of deoxoartemisinin were prepared from artemisinic acid in natural configuration.

  DOI：

  10.3987/com-99-8746

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。
• NEW SERIES OF ARTEMISININ DERIVATIVES AND PROCESS FOR PREPARATION THEREOF
  申请人：Baishya Gakul

  公开号：US20130030044A1

  公开（公告）日：2013-01-31

  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。
• 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。
• Artemisinin-Polypyrrole Conjugates: Synthesis, DNA Binding Studies and Preliminary Antiproliferative Evaluation
  作者：Louise La Pensée、Sunil Sabbani、Raman Sharma、Inder Bhamra、Emma Shore、Amy E. Chadwick、Neil G. Berry、James Firman、Nuna C. Araujo、Lília Cabral、Maria L. S. Cristiano、Cerys Bateman、Omar Janneh、Adelina Gavrila、Yi Hang Wu、Afthab Hussain、Stephen A. Ward、Paul A. Stocks、Rick Cosstick、Paul M. O'Neill

  DOI：10.1002/cmdc.201200536

  日期：2013.5

  trials against breast, colorectal and non‐small‐cell lung cancers. In an attempt to offer increased specificity, a series of hybrid artemisinin–polypyrrole minor groove binder conjugates are described. DNA binding/modelling studies and preliminary biological evaluation give insights into their mechanism of action and the potential of this strategy.

  大于其各部分的总和：青蒿素目前正处于针对乳腺癌、结直肠癌和非小细胞肺癌的 I-II 期临床试验中。为了提供更高的特异性，描述了一系列混合青蒿素-聚吡咯小沟结合剂偶联物。DNA 结合/建模研究和初步生物学评估可以深入了解其作用机制和该策略的潜力。
• Synthesis and Antimalarial Activities of 12.beta.-Allyldeoxoartemisinin and Its Derivatives
  作者：Yu Ming Pu、Herman Ziffer

  DOI：10.1021/jm00004a007

  日期：1995.2

  Synthesis of 12 beta-allyldeoxoartemisinin from dihydroartemisinin and subsequent transformations to other 12 beta-alkyldeoxoartemisinins are described. All compounds were tested in vitro versus two drug-resistant strains (Plasmodium falciparum) of malaria. The in vivo activity and toxicity of the most active compound, 12 beta-propyldeoxoartemisinin, were comparable to that of arteether.

  描述了由二氢青蒿素合成12β-烯丙基脱氧青蒿素和随后转化为其他12β-烷基脱氧青蒿素的方法。所有化合物均在体外与两种疟疾耐药菌株（恶性疟原虫）进行了测试。最活泼的化合物12β-丙基脱氧青蒿素的体内活性和毒性可与Arteether媲美。