TF 27

• 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: TF 27
• 英文别名: 4-O-[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl] 1-O-[3-[(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]-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]methyl]propyl] butanedioate
• 化学式: C₅₃H₈₀O₁₆
• 分子量: 973.209
• InChiKey: WZLHBSQLMMYTKF-BPYQGHQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  69
• 可旋转键数：
  12
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  163
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  青蒿琥酯 、 isobu-OH 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以100%的产率得到TF 27
  参考文献：
  名称：

  Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.07.048

文献信息

• ARTEMISININ-DERIVED TRIMERS AND TETRAMERS AND THEIR USE THEREOF
  申请人：ZHAO MING

  公开号：US20210079011A1

  公开（公告）日：2021-03-18

  The present disclosure provides compositions comprising artemisinin-derived trimers and tetramers; methods of preparing these compositions; and methods for their use as medicaments.
• 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.