(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-amino-5-((2-ethoxyethyl)selanyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate | 1233477-11-6

• 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: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-amino-5-((2-ethoxyethyl)selanyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS: 1233477-11-6
• 化学式: C₁₉H₂₇N₃O₉Se
• 分子量: 520.398
• InChiKey: WAASKIILPPTNKV-GFOCRRMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  158.27
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-ethoxyethaneseleninic acid 、 4-N-2',3',5'-O-四乙酰胞苷 在 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以46%的产率得到(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(4-amino-5-((2-ethoxyethyl)selanyl)-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate
  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