5-[3-(3-Fluoro-phenoxy)-benzyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one | 156176-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[3-(3-Fluoro-phenoxy)-benzyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: 5-[[3-(3-fluorophenoxy)phenyl]methyl]-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 156176-04-4
• 化学式: C₁₇H₁₃FN₂O₂S
• 分子量: 328.367
• InChiKey: FIARFJZWWKKNEF-UHFFFAOYSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[3-(3-Fluoro-phenoxy)-benzyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 溶剂黄146 、 氯乙酸 作用下， 反应 6.0h， 以91%的产率得到5-[3-(3-fluorophenoxy)benzyl]uracil
  参考文献：
  名称：

  Inhibition of Uridine Phosphorylase. Synthesis and Structure−Activity Relationships of Aryl-Substituted 1-((2-Hydroxyethoxy)methyl)-5-(3-phenoxybenzyl)uracil

  摘要：

  Structure-activity relationship studies on a series of 1-((2-hydroxyethoxy)methyl)-5-(3(substituted-phenoxy)benzyl)uracils as inhibitors of murine liver uridine phosphorylase have led to compounds with IC(50)s as low as 1.4 nM. The two most potent compounds, 10j (3-cyanophenoxy) and 11f (3-chlorophenoxy) were tested in vivo for effects on steady-state concentrations of circulating uridine in mice and rats. Both compounds were substantially more efficacious than BAU (5-benzylacyclouridine) both in vitro and in vivo.

  DOI：

  10.1021/jm960688j
• 作为产物：
  描述：

  3-氟苯酚 在 platinum(IV) oxide palladium diacetate 、 potassium tert-butylate 、 氢气 、 sodium methylate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 乙腈 为溶剂， 25.0~180.0 ℃ 、206.84 kPa 条件下， 反应 61.0h， 生成 5-[3-(3-Fluoro-phenoxy)-benzyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  Inhibition of Uridine Phosphorylase. Synthesis and Structure−Activity Relationships of Aryl-Substituted 1-((2-Hydroxyethoxy)methyl)-5-(3-phenoxybenzyl)uracil

  摘要：

  Structure-activity relationship studies on a series of 1-((2-hydroxyethoxy)methyl)-5-(3(substituted-phenoxy)benzyl)uracils as inhibitors of murine liver uridine phosphorylase have led to compounds with IC(50)s as low as 1.4 nM. The two most potent compounds, 10j (3-cyanophenoxy) and 11f (3-chlorophenoxy) were tested in vivo for effects on steady-state concentrations of circulating uridine in mice and rats. Both compounds were substantially more efficacious than BAU (5-benzylacyclouridine) both in vitro and in vivo.

  DOI：

  10.1021/jm960688j

文献信息

• Inhibition of Uridine Phosphorylase. Synthesis and Structure−Activity Relationships of Aryl-Substituted 1-((2-Hydroxyethoxy)methyl)-5-(3-phenoxybenzyl)uracil
  作者：G. Faye Orr、David L. Musso、James L. Kelley、Suzanne S. Joyner、Stephen T. Davis、David P. Baccanari

  DOI：10.1021/jm960688j

  日期：1997.4.1

  Structure-activity relationship studies on a series of 1-((2-hydroxyethoxy)methyl)-5-(3(substituted-phenoxy)benzyl)uracils as inhibitors of murine liver uridine phosphorylase have led to compounds with IC(50)s as low as 1.4 nM. The two most potent compounds, 10j (3-cyanophenoxy) and 11f (3-chlorophenoxy) were tested in vivo for effects on steady-state concentrations of circulating uridine in mice and rats. Both compounds were substantially more efficacious than BAU (5-benzylacyclouridine) both in vitro and in vivo.