3'-O-(3-trimethylammoniumpropyl)thymidine iodide

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-O-(3-trimethylammoniumpropyl)thymidine iodide
• 英文别名: 3-[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxypropyl-trimethylazanium;iodide
• 化学式: C₁₆H₂₈N₃O₅*I
• 分子量: 469.32
• InChiKey: ANUMLMRWOLDEPZ-SOIKFHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.39
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5'-O-tritylthymidine 在 sodium hydride 、 溶剂黄146 作用下， 反应 14.17h， 生成 3'-O-(3-trimethylammoniumpropyl)thymidine iodide
  参考文献：
  名称：

  Synthesis and investigation of antiviral activity of 3?-O-(aminoalkyl)-thymidines and their quaternary ammonium salts

  摘要：

  Alkylation of 5'-O-tritylthymidine with dialkylaminoalkyl chlorides in the presence of sodium hydride yields 3'-O-dialkylaminoalkyl-5'-O-tritylthymidine derivatives 2 which were treated with an excess of iodomethane to afford the corresponding quaternary ammonium derivatives 3. Deprotected nucleosides 4 and 6 were obtained by refluxing 3 and 2, respectively, in 80% acetic acid. When the compounds 2-4 and 6 were investigated for activity against HSV and HIV, the trityl derivatives 2a and 2c were found active against HSV.

  DOI：

  10.1007/bf01277631

文献信息

• Synthesis and investigation of antiviral activity of 3?-O-(aminoalkyl)-thymidines and their quaternary ammonium salts
  作者：S. El-Kousy、E. B. Pedersen、C. Nielsen

  DOI：10.1007/bf01277631

  日期：1994.6

  Alkylation of 5'-O-tritylthymidine with dialkylaminoalkyl chlorides in the presence of sodium hydride yields 3'-O-dialkylaminoalkyl-5'-O-tritylthymidine derivatives 2 which were treated with an excess of iodomethane to afford the corresponding quaternary ammonium derivatives 3. Deprotected nucleosides 4 and 6 were obtained by refluxing 3 and 2, respectively, in 80% acetic acid. When the compounds 2-4 and 6 were investigated for activity against HSV and HIV, the trityl derivatives 2a and 2c were found active against HSV.