3'-O-<2-(N-methylpyrrolidinium)ethyl>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-<2-(N-methylpyrrolidinium)ethyl>thymidine iodide
• 英文别名: 3'-O-[2-(N-methylpyrrolidinium)ethyl]thymidine iodide；1-[(2R,4S,5R)-5-(hydroxymethyl)-4-[2-(1-methylpyrrolidin-1-ium-1-yl)ethoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione;iodide
• 化学式: C₁₇H₂₈N₃O₅*I
• 分子量: 481.331
• InChiKey: BFQUJBBQZPUBEM-ONAKXNSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.25
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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 9.17h， 生成 3'-O-<2-(N-methylpyrrolidinium)ethyl>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