2',3'-didehydro-2',3'-dideoxy-5-[N-(prop-2-ynyl)aminomethyl]-uridine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 2',3'-didehydro-2',3'-dideoxy-5-[N-(prop-2-ynyl)aminomethyl]-uridine
• 英文别名: 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-[(prop-2-ynylamino)methyl]pyrimidine-2,4-dione
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: UKMZNKIFHWNDIB-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  炔丙胺 、 5-Chloromethyl-1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以30 mg的产率得到2',3'-didehydro-2',3'-dideoxy-5-[N-(prop-2-ynyl)aminomethyl]-uridine
  参考文献：
  名称：

  Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms

  摘要：

  A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of "different sizes". Reactions of the 2',3'-didehydro2',3'-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1.

  DOI：

  10.1080/15257770008033040