(3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-((Z)-4-hydroxybut-2-enoxy)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin | 1203603-32-0

• 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: (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-((Z)-4-hydroxybut-2-enoxy)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin
• 英文别名: cis-2-Butene-1,4-diol B-DHA acetal monomer；(Z)-4-[[(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]oxy]but-2-en-1-ol
• CAS: 1203603-32-0
• 化学式: C₁₉H₃₀O₆
• 分子量: 354.444
• InChiKey: LLYSKOKOPFAQNE-LBVXNRGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 dihydroartemisinin 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以22.2%的产率得到(3R,3'R,5aS,5a'S,6R,6'R,8aS,8a'S,9R,9'R,10S,10'S,12R,12'R,12aR,12a'R)-10,10'-[1,4-(Z)-but-2-enediylbis(oxy)]bis[decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin]
  参考文献：
  名称：

  Antiprotozoal, anticancer and antimicrobial activities of dihydroartemisinin acetal dimers and monomers

  摘要：

  Nine dihydroartemisinin acetal dimers (6-14) with diversely functionalized linker units were synthesized and tested for in vitro antiprotozoal, anticancer and antimicrobial activity. Compounds 6, 7 and 11 [IC50: 3.0-6.7 nM (D6) and 4.2-5.9 nM (W2)] were appreciably more active than artemisinin (1) [IC50: 32.9 nM (D6) and 42.5 nM (W2)] against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of the malaria parasite, Plasmodium falciparum. Compounds 10, 13 and 14 displayed enhanced anticancer activity in a number of cell lines compared to the control drug, doxorubicin. The antifungal activity of 7 and 12 against Cryptococcus neoformans (IC50: 0.16 and 0.55 mu M, respectively) was also higher compared to the control drug, amphotericin B. The antileishmanial and antibacterial activities were marginal. A number of dihydroartemisinin acetal monomers (15-17) and a trimer (18) were isolated as byproducts from the dimer synthesis and were also tested for biological activity. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.019

文献信息

• Antiprotozoal, anticancer and antimicrobial activities of dihydroartemisinin acetal dimers and monomers
  作者：Desmond Slade、Ahmed M. Galal、Waseem Gul、Mohamed M. Radwan、Safwat A. Ahmed、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Samir A. Ross、Mahmoud A. ElSohly

  DOI：10.1016/j.bmc.2009.10.019

  日期：2009.12

  Nine dihydroartemisinin acetal dimers (6-14) with diversely functionalized linker units were synthesized and tested for in vitro antiprotozoal, anticancer and antimicrobial activity. Compounds 6, 7 and 11 [IC50: 3.0-6.7 nM (D6) and 4.2-5.9 nM (W2)] were appreciably more active than artemisinin (1) [IC50: 32.9 nM (D6) and 42.5 nM (W2)] against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of the malaria parasite, Plasmodium falciparum. Compounds 10, 13 and 14 displayed enhanced anticancer activity in a number of cell lines compared to the control drug, doxorubicin. The antifungal activity of 7 and 12 against Cryptococcus neoformans (IC50: 0.16 and 0.55 mu M, respectively) was also higher compared to the control drug, amphotericin B. The antileishmanial and antibacterial activities were marginal. A number of dihydroartemisinin acetal monomers (15-17) and a trimer (18) were isolated as byproducts from the dimer synthesis and were also tested for biological activity. (c) 2009 Elsevier Ltd. All rights reserved.