4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-ethoxyethylselanyl)pyrimidin-2-one | 1233477-15-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-ethoxyethylselanyl)pyrimidin-2-one
• CAS: 1233477-15-0
• 化学式: C₁₃H₂₁N₃O₆Se
• 分子量: 394.286
• InChiKey: CYBIAFBOLVAEFK-UGKPPGOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.78
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-amino-5-((2-ethoxyethyl)selanyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(2-ethoxyethylselanyl)pyrimidin-2-one
  参考文献：
  名称：

  Electrophilic Aromatic Selenylation: New OPRT Inhibitors

  摘要：

  2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.

  DOI：

  10.1021/ol1010032

文献信息

• Electrophilic Aromatic Selenylation: New OPRT Inhibitors
  作者：Mohannad Abdo、Yong Zhang、Vern L. Schramm、Spencer Knapp

  DOI：10.1021/ol1010032

  日期：2010.7.2

  2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.