10α-dihydroartemisinyl 2-phenylacetate

• 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: 10α-dihydroartemisinyl 2-phenylacetate
• 英文别名: [(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] 2-phenylacetate
• 化学式: C₂₃H₃₀O₆
• 分子量: 402.488
• InChiKey: PBLOWEXHKMBUGD-DFIIIMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dihydroartemisinin 、 苯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以40.1%的产率得到10α-dihydroartemisinyl 2-phenylacetate
  参考文献：
  名称：

  Antimalarial activity of 10-alkyl/aryl esters and -aminoethylethers of artemisinin

  摘要：

  A series of n-alkyl/aryl esters were synthesized and their in vitro antiplasmodial activity was measured alongside that of previously synthesized aminoethylethers of artemisinin ozonides against various strains of Plasmodium falciparum. The cytotoxicity against human cell lines was also assessed. The esters were synthesized in a one-step reaction by derivatization on carbon C-10 of dihydroartemisinin. Both classes were active against both the 3D7 and K1 strains of P. falciparum, with all compounds being significantly more potent than artemether against both strains. The majority of compounds possessed potency either comparable or more than artesunate with a high degree of selectivity towards the parasitic cells. The 10 alpha-n-propyl 11 and 10 alpha-benzyl 18 esters were the most potent of all synthesized ozonides, possessing a moderate (similar to 3-fold) and significant (22- and 12-fold, respectively) potency increases against the 3D7 and K1 strains, respectively, in comparison with artesunate. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2012.10.002

文献信息

• Antimalarial activity of 10-alkyl/aryl esters and -aminoethylethers of artemisinin
  作者：Theunis T. Cloete、Henk J. Krebs、Julie A. Clark、Michele C. Connelly、Amy Orcutt、Martina S. Sigal、R. Kiplin Guy、David D. N’Da

  DOI：10.1016/j.bioorg.2012.10.002

  日期：2013.2

  A series of n-alkyl/aryl esters were synthesized and their in vitro antiplasmodial activity was measured alongside that of previously synthesized aminoethylethers of artemisinin ozonides against various strains of Plasmodium falciparum. The cytotoxicity against human cell lines was also assessed. The esters were synthesized in a one-step reaction by derivatization on carbon C-10 of dihydroartemisinin. Both classes were active against both the 3D7 and K1 strains of P. falciparum, with all compounds being significantly more potent than artemether against both strains. The majority of compounds possessed potency either comparable or more than artesunate with a high degree of selectivity towards the parasitic cells. The 10 alpha-n-propyl 11 and 10 alpha-benzyl 18 esters were the most potent of all synthesized ozonides, possessing a moderate (similar to 3-fold) and significant (22- and 12-fold, respectively) potency increases against the 3D7 and K1 strains, respectively, in comparison with artesunate. (C) 2012 Elsevier Inc. All rights reserved.