O-acetyldihydroartemisinin

• 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: O-acetyldihydroartemisinin
• 英文别名: [(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] acetate
• 化学式: C₁₇H₂₆O₆
• 分子量: 326.39
• InChiKey: WNQITGRHOWFLEA-ROLURPKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-acetyldihydroartemisinin 在 sodium peroxoborate tetrahydrate 、 dimethyl sulfide borane 、 四氯化锡 作用下， 生成 3-(10-deoxoartemisin-10-yl)propanoic acid
  参考文献：
  名称：

  [EN] MONOMERIC TRIOXANE AMIDE SULFUR COMPOUNDS
  [FR] COMPOSÉS DE SOUFRE D'AMIDE DE TRIOXANE MONOMÈRE

  摘要：

  公开号：

  WO2012142575A3
• 作为产物：
  描述：

  乙酸酐 、 青蒿素 在 sodium tetrahydroborate 、 cation exchange resin 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 O-acetyldihydroartemisinin
  参考文献：
  名称：

  [EN] SINGLE POT CONVERSION OF ARTEMISININ TO ARTESUNIC ACID
  [FR] CONVERSION D'ARTEMISININE EN ACIDE ARTESUNIQUE DANS UN RECIPIENT UNIQUE

  摘要：

  本发明提供了一种从青蒿素制备青蒿酸的单锅法工艺，包括在室温下还原后酯化还原产物的步骤。

  公开号：

  WO2004050661A1

文献信息

• Modular Synthesis and in Vitro and in Vivo Antimalarial Assessment of C-10 Pyrrole Mannich Base Derivatives of Artemisinin
  作者：Bénédicte Pacorel、Suet C. Leung、Andrew V. Stachulski、Jill Davies、Livia Vivas、Hollie Lander、Stephen A. Ward、Marcel Kaiser、Reto Brun、Paul M. O’Neill

  DOI：10.1021/jm901216v

  日期：2010.1.28

  In two steps from dihydroartemisinin, a small array of 16 semisynthetic C-10 pyrrole Mannich artemisinin derivatives (7a−p) have been prepared in moderate to excellent yield. In vitro analysis against both chloroquine sensitive and resistant strains has demonstrated that these analogues have nanomolar antimalarial activity, with several compounds being more than 3 times more potent than the natural

  在二氢青蒿素的两个步骤中，已制备了少量的16种半合成C-10吡咯曼尼希青蒿素衍生物（7a-p），产率中等至极好。对氯喹敏感和耐药菌株的体外分析表明，这些类似物具有纳摩尔抗疟活性，几种化合物的功效比天然产物青蒿素高3倍以上。除了有效的抗疟特性外，这些分子还具有很高的体外治疗指数。体外和体内活性的最佳曼尼希侧链取代分析表明，吗啉和氮-甲基哌嗪曼尼希侧链在彼得的4天试验中在体外和体内均提供了具有最佳活性的类似物。
• Access to new highly potent antileukemia, antiviral and antimalarial agents via hybridization of natural products (homo)egonol, thymoquinone and artemisinin
  作者：Aysun Çapcı Karagöz、Christoph Reiter、Ean-Jeong Seo、Lisa Gruber、Friedrich Hahn、Maria Leidenberger、Volker Klein、Frank Hampel、Oliver Friedrich、Manfred Marschall、Barbara Kappes、Thomas Efferth、Svetlana B. Tsogoeva

  DOI：10.1016/j.bmc.2018.05.041

  日期：2018.7

  Hybridization of natural products has high potential to further improve their activities and may produce synergistic effects between linked pharmacophores. Here we report synthesis of nine new hybrids of natural products egonol, homoegonol, thymoquinone and artemisinin and evaluation of their activities against P. falciparum 3D7 parasites, human cytomegalovirus, sensitive and multidrug-resistant human

  天然产物的杂交具有进一步改善其活性的高潜力，并可能在连接的药效团之间产生协同作用。在这里，我们报告了九种新的天然产物杂香油，高胡香酚，胸腺醌和青蒿素的杂种的合成，并评估了它们对抗恶性疟原虫3D7寄生虫，人类巨细胞病毒，敏感和多药耐药性人类白血病细胞的活性。大多数新杂种在抗疟疾，抗病毒和抗白血病的活性方面超过其母体化合物，并且在某些情况下显示出更高的体外活性疗效优于临床上使用的参考药物氯喹，更昔洛韦和阿霉素。综合起来，我们的发现强调了这些杂种的高效力，并鼓励在应用药理学研究中进一步使用杂交概念。
• 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.
• Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities
  作者：Christoph Reiter、Tony Fröhlich、Lisa Gruber、Corina Hutterer、Manfred Marschall、Cornelia Voigtländer、Oliver Friedrich、Barbara Kappes、Thomas Efferth、Svetlana B. Tsogoeva

  DOI：10.1016/j.bmc.2015.07.048

  日期：2015.9

  New pharmaceutically active compounds can be obtained by modification of existing drugs to access more effective agents in the wake of drug resistance amongst others. To achieve this goal the concept of hybridization was established during the last decade. We employed this concept by coupling two artemisinin-derived precursors to obtain dimers or trimers with increased in vitro activity against Plasmodium falciparum 3D7 strain, leukemia cells (CCRF-CEM and multidrug-resistant subline CEM/ADR5000) and human cytomegalovirus (HCMV). Dimer 4 (IC50 of 2.6 nM) possess superior antimalarial activity compared with its parent compound artesunic acid (3) (IC50 of 9.0 nM). Dimer 5 and trimers 6 and 7 display superior potency against both leukemia cell lines (IC50 up to 0.002 mu M for CCRF-CEM and IC50 up to 0.20 mu M for CEM/ADR5000) and are even more active than clinically used doxorubicin (IC50 1.61 mu M for CEM/ADR5000). With respect to anti-HCMV activity, trimer 6 is the most efficient hybrid (IC50 0.04 mu M) outperforming ganciclovir (IC50 2.6 mu M), dihydroartemisinin (IC50 > 10 mu M) and artesunic acid (IC50 3.8 mu M). (C) 2015 Elsevier Ltd. All rights reserved.
• CN115109069
  申请人：——

  公开号：——

  公开（公告）日：——