(RS)-3-(thymin-1-yl)-N-pyrrolidinylmethylphosphonic acid | 1219028-38-2

• 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: (RS)-3-(thymin-1-yl)-N-pyrrolidinylmethylphosphonic acid
• 英文别名: [3-(5-Methyl-2,4-dioxopyrimidin-1-yl)pyrrolidin-1-yl]methylphosphonic acid
• CAS: 1219028-38-2
• 化学式: C₁₀H₁₆N₃O₅P
• 分子量: 289.228
• InChiKey: BTJHOZXEILIZQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  diisopropyl ((3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)pyrrolidin-1-yl)methyl)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， 以75 mg的产率得到(RS)-3-(thymin-1-yl)-N-pyrrolidinylmethylphosphonic 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

文献信息

• Structural diversity of nucleoside phosphonic acids as a key factor in the discovery of potent inhibitors of rat T-cell lymphoma thymidine phosphorylase
  作者：Petr Kočalka、Dominik Rejman、Václav Vaněk、Markéta Rinnová、Ivana Tomečková、Šárka Králíková、Magdalena Petrová、Ondřej Páv、Radek Pohl、Miloš Buděšínský、Radek Liboska、Zdeněk Točík、Natalya Panova、Ivan Votruba、Ivan Rosenberg

  DOI：10.1016/j.bmcl.2009.12.081

  日期：2010.2

  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.