1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]diselanyl]pyrimidine-2,4-dione | 1233477-36-5

• 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: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]diselanyl]pyrimidine-2,4-dione
• CAS: 1233477-36-5
• 化学式: C₁₈H₂₂N₄O₁₂Se₂
• 分子量: 644.312
• InChiKey: IWNDLAMETQQENB-FRLUBHLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.12
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  239
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (2R,2'R,3R,3'R,4R,4'R,5R,5'R)-(diselanediylbis(2,4-dioxo-3,4-dihydropyrimidine-5,1(2H)-diyl))bis(5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl) tetraacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]diselanyl]pyrimidine-2,4-dione
  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