4-amino-1-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidin-2-one | 1203489-30-8

• 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: 4-amino-1-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidin-2-one
• CAS: 1203489-30-8
• 化学式: C₁₂H₁₄FN₃O₃
• 分子量: 267.26
• InChiKey: ACAKAKLATTWZAP-SZEHBUNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.37
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-amino-1-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidin-2-one 在 水 、 三氟乙酸 作用下， 反应 2.5h， 以42%的产率得到4-amino-1-(2-fluoro-4,5-dihydroxy-cyclopent-2-enyl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Truncated Fluorocyclopentenyl Pyrimidines as S-Adenosylhomocysteine Hydrolase Inhibitors

  摘要：

  On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl Pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 mu M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, Leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 mu M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.

  DOI：

  10.1080/15257770903054316
• 作为产物：
  描述：

  1-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidine-2,4-dione 在 吡啶 、 1H-1,2,4-三唑 、 4-氯苯基二氯磷酸酯 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以66%的产率得到4-amino-1-(5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Truncated Fluorocyclopentenyl Pyrimidines as S-Adenosylhomocysteine Hydrolase Inhibitors

  摘要：

  On the basis of inhibitory activity of truncated cyclopentenyl cytosine against S-adenosylhomocysteine hydrolase (SAH), its fluorocyclopentenyl Pyrimidine derivatives were efficiently synthesized from D-ribose via electrophilic fluorination as a key step. The final nucleosides were evaluated for SAH inhibitory activity, among which the uracil derivative 9 showed significant inhibitory activity (IC50 = 8.53 mu M). They were also evaluated for cytotoxic effects in several human cancer cell lines such as fibro sarcoma, stomach cancer, Leukemia, and colon cancer, but they did not show any cytotoxic effects up to 100 mu M, indicating that 4'-hydroxymethyl groups are essential for the anticancer activity.

  DOI：

  10.1080/15257770903054316