10-hydroxy-1-[(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]decan-2-one | 851380-70-6

• 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: 10-hydroxy-1-[(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]decan-2-one
• CAS: 851380-70-6
• 化学式: C₂₅H₄₂O₆
• 分子量: 438.605
• InChiKey: BSRHEEHRXPTNKB-STRFBEOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10-hydroxy-1-[(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]decan-2-one 在 jones reagent 作用下， 以 丙酮 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Synthesis and Cytotoxicity Studies of Artemisinin Derivatives Containing Lipophilic Alkyl Carbon Chains

  摘要：

  Cytotoxic artermisinin derivatives have been synthesized by a modular approach of '' artemisinin + linker + lipophilic alkyl carbon chain ''. A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC50 = 97 mu M), up to 200-fold more potent cytotoxicity (IC50 = 0.46 mu M) could be achieved by attachment of a C14H29 carbon chain to artemisinin via an amide linker.

  DOI：

  10.1021/ol050230o
• 作为产物：
  描述：

  双氢青蒿素 在 吡啶 、 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium periodate 、 重铬酸吡啶 、 对甲苯磺酸 、 magnesium 、 zinc(II) chloride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 3.0h， 生成 10-hydroxy-1-[(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]decan-2-one
  参考文献：
  名称：

  Synthesis and Cytotoxicity Studies of Artemisinin Derivatives Containing Lipophilic Alkyl Carbon Chains

  摘要：

  Cytotoxic artermisinin derivatives have been synthesized by a modular approach of '' artemisinin + linker + lipophilic alkyl carbon chain ''. A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC50 = 97 mu M), up to 200-fold more potent cytotoxicity (IC50 = 0.46 mu M) could be achieved by attachment of a C14H29 carbon chain to artemisinin via an amide linker.

  DOI：

  10.1021/ol050230o

文献信息

• Synthesis and Cytotoxicity Studies of Artemisinin Derivatives Containing Lipophilic Alkyl Carbon Chains
  作者：Yungen Liu、Vincent Kam-Wai Wong、Ben Chi-Bun Ko、Man-Kin Wong、Chi-Ming Che

  DOI：10.1021/ol050230o

  日期：2005.4.14

  Cytotoxic artermisinin derivatives have been synthesized by a modular approach of '' artemisinin + linker + lipophilic alkyl carbon chain ''. A strong correlation between the length of the carbon chains and the cytotoxicities against human hepatocellular carcinoma (HepG2) was revealed. Notably, compared with artemisinin (IC50 = 97 mu M), up to 200-fold more potent cytotoxicity (IC50 = 0.46 mu M) could be achieved by attachment of a C14H29 carbon chain to artemisinin via an amide linker.