(+/-)-5-[4,4-bis-(hydroxymethyl)-cyclopent-2-enyl]uracil | 1193397-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (+/-)-5-[4,4-bis-(hydroxymethyl)-cyclopent-2-enyl]uracil
• 英文别名: 5-[4,4-bis(hydroxymethyl)cyclopent-2-en-1-yl]-1H-pyrimidine-2,4-dione
• CAS: 1193397-16-8
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: DPJMIWCRHQTTOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+/-)-5-[4,4-bis-(tert-butyldimethylsilanyloxymethyl)cyclopent-2-enyl]uracil 在 四丁基氟化铵 、 甲醇 、 silica gel 作用下， 以 四氢呋喃 、 乙腈 、 二氯甲烷 为溶剂， 以76%的产率得到(+/-)-5-[4,4-bis-(hydroxymethyl)-cyclopent-2-enyl]uracil
  参考文献：
  名称：

  Synthesis and Anti-Hiv Activity of 4′-Modified Cyclopentenyl PyrimidineC-Nucleosides

  摘要：

  Novel syntheses of 4-modified cyclopentenyl pyrimidine C-nucleosides were performed via C-C bond formation using S(N)2 alkylation via the key intermediate mesylates 6 and 16, which were prepared,from acyclic ketone derivatives. When antiviral evaluation of synthesized, compound was performed against various viruses such as HIV-1, HSV-1 and HSV-2, isocytidine analogue 20 showed, moderate anti-HIV activity in CEM cell line (EC50 = 13.1 mu mol).

  DOI：

  10.1080/15257770902946058

文献信息

• Synthesis and Anti-Hiv Activity of 4′-Modified Cyclopentenyl Pyrimidine<i>C</i>-Nucleosides
  作者：Lian Jin Liu、Joon Hee Hong

  DOI：10.1080/15257770902946058

  日期：2009.5.22

  Novel syntheses of 4-modified cyclopentenyl pyrimidine C-nucleosides were performed via C-C bond formation using S(N)2 alkylation via the key intermediate mesylates 6 and 16, which were prepared,from acyclic ketone derivatives. When antiviral evaluation of synthesized, compound was performed against various viruses such as HIV-1, HSV-1 and HSV-2, isocytidine analogue 20 showed, moderate anti-HIV activity in CEM cell line (EC50 = 13.1 mu mol).