diisopropyl (3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidine-1-carbonothioyl)phosphonate | 1219028-46-2

• 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: diisopropyl (3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidine-1-carbonothioyl)phosphonate
• CAS: 1219028-46-2
• 化学式: C₁₆H₂₆N₃O₅PS
• 分子量: 403.439
• InChiKey: QNFXIXUVUXWZMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  93.63
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diisopropyl (3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidine-1-carbonothioyl)phosphonate 在 三甲基溴硅烷 、 四乙基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [3-(5-Methyl-2,4-dioxopyrimidin-1-yl)pyrrolidine-1-carbothioyl]phosphonic acid 、 [3-(5-Methyl-2,4-dioxopyrimidin-1-yl)pyrrolidine-1-carbothioyl]phosphonic acid
  参考文献：
  名称：

  Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase

  摘要：

  Structurally diverse, sugar-modified, thymine-containing nucleoside phosphonic acids were evaluated for their ability to inhibit thymidine phosphorylase (TP, EC 2.4.2.4) purified from spontaneous T-cell lymphomas of an inbred Sprague-Dawley rat strain. From a large set of tested compounds, among them a number of pyrrolidine-based derivatives, 10 nucleotide analogues with IC50 values below 1 mu M were selected. Out of them, four compounds strongly inhibited the enzyme with IC50 values lying in a range of 11-45 nM. These most potent compounds might be bi-substrate analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.081
• 作为产物：
  描述：

  (RS)-3-(thymin-1-yl)pyrrolidine hydrochloride 、 methyl [(diisopropoxy)phosphinyl]dithioformate 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 diisopropyl (3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidine-1-carbonothioyl)phosphonate
  参考文献：
  名称：

  Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase

  摘要：

  Structurally diverse, sugar-modified, thymine-containing nucleoside phosphonic acids were evaluated for their ability to inhibit thymidine phosphorylase (TP, EC 2.4.2.4) purified from spontaneous T-cell lymphomas of an inbred Sprague-Dawley rat strain. From a large set of tested compounds, among them a number of pyrrolidine-based derivatives, 10 nucleotide analogues with IC50 values below 1 mu M were selected. Out of them, four compounds strongly inhibited the enzyme with IC50 values lying in a range of 11-45 nM. These most potent compounds might be bi-substrate analogues. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.081