N-hexadecyl-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]acetamide | 851380-87-5

• 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: N-hexadecyl-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]acetamide
• CAS: 851380-87-5
• 化学式: C₃₃H₅₉NO₅
• 分子量: 549.835
• InChiKey: OAQCYTVZULNTKF-ZYBNLUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  39
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-hexadecyl-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]acetamide 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以85%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 、 Oxone 、 sodium periodate 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.5h， 生成 N-hexadecyl-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]acetamide
  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.