1-<(2-amino-4-hydroxy-5-nitropyrimidin-6-yl)amino>-4--2,2-(ethylenedioxy)butane | 83704-96-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-<(2-amino-4-hydroxy-5-nitropyrimidin-6-yl)amino>-4--2,2-(ethylenedioxy)butane
• CAS: 83704-96-5
• 化学式: C₂₁H₂₉F₃N₆O₈
• 分子量: 550.492
• InChiKey: RBRXUKFIMRCAGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  192.01
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-<(2-amino-4-hydroxy-5-nitropyrimidin-6-yl)amino>-4--2,2-(ethylenedioxy)butane 在 盐酸 、 三氟乙酸 作用下， 以94%的产率得到1-<(2-amino-4-hydroxy-5-nitropyrimidin-6-yl)amino>-4-butan-2-one
  参考文献：
  名称：

  Folate analogs. 20. Synthesis and antifolate activity of 1',2',3',4',5',6'-hexahydrohomofolic acid

  摘要：

  The synthesis of 1',2',3',4',5',6'-hexahydrohomofolic acid (3), a close analogue of homofolic acid (2), has been carried out by replacement of the benzene ring of 2 with a cyclohexane ring. The synthetic methods employed here were based on the Boon-Leigh strategy to obtain products with unambiguous structures. Based on a number of chemical and spectral observations, a tentative cis stereochemistry was assigned to the 1,4-substituents of the cyclohexane ring of both the homopteroate analogue 13 and the target compound 3. We investigated hexahydrohomopteroic acid (13), hexahydrohomofolic acid (3), and their 7,8-dihydro and d,l-5,6,7,8-tetrahydro derivatives for antifolate activity employing several biological test systems. The dihydro and tetrahydro derivatives of both 13 and 3 were active against Streptococcus faecium, whereas they were inactive against Lactobacillus casei. These compounds were neither substrates nor inhibitors of L. casei dihydrofolate reductase or thymidylate synthase.

  DOI：

  10.1021/jm00356a004
• 作为产物：
  描述：

  1-azido-4-butane-2-one 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 28.0h， 生成 1-<(2-amino-4-hydroxy-5-nitropyrimidin-6-yl)amino>-4--2,2-(ethylenedioxy)butane
  参考文献：
  名称：

  Folate analogs. 20. Synthesis and antifolate activity of 1',2',3',4',5',6'-hexahydrohomofolic acid

  摘要：

  The synthesis of 1',2',3',4',5',6'-hexahydrohomofolic acid (3), a close analogue of homofolic acid (2), has been carried out by replacement of the benzene ring of 2 with a cyclohexane ring. The synthetic methods employed here were based on the Boon-Leigh strategy to obtain products with unambiguous structures. Based on a number of chemical and spectral observations, a tentative cis stereochemistry was assigned to the 1,4-substituents of the cyclohexane ring of both the homopteroate analogue 13 and the target compound 3. We investigated hexahydrohomopteroic acid (13), hexahydrohomofolic acid (3), and their 7,8-dihydro and d,l-5,6,7,8-tetrahydro derivatives for antifolate activity employing several biological test systems. The dihydro and tetrahydro derivatives of both 13 and 3 were active against Streptococcus faecium, whereas they were inactive against Lactobacillus casei. These compounds were neither substrates nor inhibitors of L. casei dihydrofolate reductase or thymidylate synthase.

  DOI：

  10.1021/jm00356a004