5-(羟基甲基)-1-[(2R,5S)-5-(羟基甲基)-2,5-二氢呋喃-2-基]嘧啶-2,4-二酮 | 158532-72-0

• 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
• 中文名称: 5-(羟基甲基)-1-[(2R,5S)-5-(羟基甲基)-2,5-二氢呋喃-2-基]嘧啶-2,4-二酮
• 英文名称: 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyl-uridine
• 英文别名: 2',3'-didehydro-2',3'-dideoxy-5-hydroxymethyluridine；2',3'-didehydro-2',3-dideoxy-5-hydroxymethyl-uridine；5-Hydroxy-d4T；5-(hydroxymethyl)-1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 158532-72-0
• 化学式: C₁₀H₁₂N₂O₅
• 分子量: 240.216
• InChiKey: KFMBQLBWJUMPQJ-JGVFFNPUSA-N

物化性质

• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(羟基甲基)-1-[(2R,5S)-5-(羟基甲基)-2,5-二氢呋喃-2-基]嘧啶-2,4-二酮 在 4-二甲氨基吡啶 、 三甲基氯硅烷 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 58.0h， 生成 2',3'-didehydro-2',3'-dideoxy-5-[N-(6-trifluoroacetylaminohexyl)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
• 作为产物：
  描述：

  5-甲基尿甙 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 5.83h， 生成 5-(羟基甲基)-1-[(2R,5S)-5-(羟基甲基)-2,5-二氢呋喃-2-基]嘧啶-2,4-二酮
  参考文献：
  名称：

  2'，3'-didehydro-2'，3'-dideoxy-5-hydroxymethyluridine的替代合成路线

  摘要：

  描述了从5-甲基尿苷和尿苷开始的核苷类似物2'，3'-didehydro-2'，3'-dideoxy-5-hydroxymethyluridine的替代合成方法。

  DOI：

  10.1016/j.tetlet.2006.09.083

文献信息

• Synthesis of Novel C-5 Substituted d4t Analogues Bearing Linker Arms as Potential Anti-HIV Agents
  作者：D. Ladurée、C. Fossey、M. Renoud-grappin、G. Fontaine、F. Camara、D. Gavriliu、A. Ciurea、A. M. Aubertin、A. Kirn

  DOI：10.1080/15257779908041592

  日期：1999.4

  This work reports the synthesis of 2',3'-didehydro-2',3'-dideoxy-thymidine analogues bearing several kinds of amino-linker arms at the C-5 position of the pyrimidine moiety. C-5 is an attractive position since a flexible chain may permit the triphosphates to be generated. The beta-D- and beta-L-d4T analogues were synthesized following a multi-step reaction from D-ribose and D-xylose, from D- and L-arabinose (towards an oxazoline ring) or from uridine and then were reacted with alkylene diamines.
• Synthesis and Antiviral Activity of C-5 Substituted Analogues of D4T Bearing Methylamino- or Methyldiamino-Linker Arms
  作者：D. Gavriliu、C. Fossey、G. Fontaine、S. Benzaria、A. Ciurea、Z. Delbederi、B. Lelong、D. Ladurée、A. M. Aubertin、A. Kirn

  DOI：10.1080/15257770008033040

  日期：2000.5

  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.
• Alternative synthetic routes to 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine
  作者：Raymond Chung、Karen S. Anderson

  DOI：10.1016/j.tetlet.2006.09.083

  日期：2006.11

  Alternative syntheses for the nucleoside analogue 2′,3′-didehydro-2′,3′-dideoxy-5-hydroxymethyluridine starting from 5-methyluridine and uridine are described.

  描述了从5-甲基尿苷和尿苷开始的核苷类似物2'，3'-didehydro-2'，3'-dideoxy-5-hydroxymethyluridine的替代合成方法。