(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-10-[(Z)-2-[3-[(Z)-2-[(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-en-10-yl]ethenyl]phenyl]ethenyl]-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-ene

• 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: (1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-10-[(Z)-2-[3-[(Z)-2-[(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-en-10-yl]ethenyl]phenyl]ethenyl]-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-ene
• 化学式: C₄₀H₅₀O₈
• 分子量: 658.832
• InChiKey: KJRZXPIIMHTZHW-XSTWJZQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  48
• 可旋转键数：
  4
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  m-xylylene-bis(triphenylphosphonium bromide) 、 10-formylanhydroartemisinin 在 lithium hexamethyldisilazane 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以27%的产率得到(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-10-[(E)-2-[3-[(E)-2-[(1R,4S,5R,8S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-en-10-yl]ethenyl]phenyl]ethenyl]-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadec-9-ene
  参考文献：
  名称：

  Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers

  摘要：

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.

  DOI：

  10.1021/jm990363d

文献信息

• Antimalarial, Antiproliferative, and Antitumor Activities of Artemisinin-Derived, Chemically Robust, Trioxane Dimers
  作者：Gary H. Posner、Poonsakdi Ploypradith、Michael H. Parker、Hardwin O'Dowd、Soon-Hyung Woo、John Northrop、Mikhail Krasavin、Patrick Dolan、Thomas W. Kensler、Suji Xie、Theresa A. Shapiro

  DOI：10.1021/jm990363d

  日期：1999.10.1

  Nine C-10 non-acetal derivatives of the natural trioxane artemisinin (1) were prepared as dimers using some novel chemistry. As designed, each dimer was stable chemically. C-10 Olefinic dimers 7 and C-10 saturated dimers 8-13 all showed good to excellent antimalarial and antiproliferative activities in vitro. Dimers 8, 10, and 12 were especially potent and selective at inhibiting growth of some human cancer cell lines in the NCI in vitro 60-cell line assay.