artemisinin acid chloride | 955035-85-5

• 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: artemisinin acid chloride
• CAS: 955035-85-5
• 化学式: C₁₇H₂₅ClO₅
• 分子量: 344.835
• InChiKey: PATUWAZGJRUAPD-LBYUOYBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  artemisinin acid chloride 、 N-(7-chloroquinolin-4-yl)propane-1,3-diamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-[3-[(7-chloroquinolin-4-yl)amino]propyl]-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]acetamide
  参考文献：
  名称：

  Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

  摘要：

  A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.013
• 作为产物：
  描述：

  2-((3R, 5aS, 6R, 8aS, 9R,10R, 12R, 12aR)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)acetic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 artemisinin acid chloride
  参考文献：
  名称：

  Semi-synthetic and synthetic 1,2,4-trioxaquines and 1,2,4-trioxolaquines: synthesis, preliminary SAR and comparison with acridine endoperoxide conjugates

  摘要：

  A novel series of semi-synthetic trioxaquines and synthetic trioxolaquines were prepared, in moderate to good yields. Antimalarial activity was evaluated against both the chloroquine-sensitive 3D7 and resistant K1 strain of Plasmodium falciparum and both series of compounds were shown to be active in the low nanomolar range. For comparison the corresponding 9-amino acridine analogues were also prepared and shown to have low nanomolar activity like their quinoline counterparts. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.013

文献信息

• Evidence for a Common Non-Heme Chelatable-Iron-Dependent Activation Mechanism for Semisynthetic and Synthetic Endoperoxide Antimalarial Drugs
  作者：Paul A. Stocks、Patrick G. Bray、Victoria E. Barton、Mohammed Al-Helal、Michael Jones、Nuna C. Araujo、Peter Gibbons、Stephen A. Ward、Ruth H. Hughes、Giancarlo A. Biagini、Jill Davies、Richard Amewu、Amy E. Mercer、Gemma Ellis、Paul M. O'Neill

  DOI：10.1002/anie.200604697

  日期：2007.8.20
• Synthesis and biological evaluation of extraordinarily potent C-10 carba artemisinin dimers against P. falciparum malaria parasites and HL-60 cancer cells
  作者：James Chadwick、Amy E. Mercer、B. Kevin Park、Richard Cosstick、Paul M. O’Neill

  DOI：10.1016/j.bmc.2008.12.017

  日期：2009.2

  A series of artemisinin dimers incorporating a metabolically stable C-10 carba-linkage have been prepared, several of which show remarkable in vitro antimalarial activity ( as low as 30 pM) versus Plasmodium falciparum and in vitro anticancer activity in the micromolar to nanomolar range versus HL-60 cell lines. (c) 2009 Elsevier Ltd. All rights reserved.
• Antitumour and antimalarial activity of artemisinin–acridine hybrids
  作者：Michael Jones、Amy E. Mercer、Paul A. Stocks、Louise J.I. La Pensée、Rick Cosstick、B. Kevin Park、Miriam E. Kennedy、Ivo Piantanida、Stephen A. Ward、Jill Davies、Patrick G. Bray、Sarah L. Rawe、Jonathan Baird、Tafadzwa Charidza、Omar Janneh、Paul M. O’Neill

  DOI：10.1016/j.bmcl.2009.02.028

  日期：2009.4

  Artemisinin-acridine hybrids were prepared and evaluated for their in vitro activity against tumour cell lines and a chloroquine sensitive strain of Plasmodium falciparum. They showed a 2-4-fold increase in activity against HL60, MDA-MB-231 and MCF-7 cells in comparison with dihydroartemisinin (DHA) and moderate antimalarial activity. Strong evidence that the compounds induce apoptosis in HL60 cells was obtained by flow cytometry, which indicated accumulation of cells in the G1 phase of the cell cycle. (C) 2009 Elsevier Ltd. All rights reserved.