diethyl ((((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate | 1365532-71-3

• 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: diethyl ((((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate
• CAS: 1365532-71-3
• 化学式: C₁₉H₂₅N₂O₇PSe
• 分子量: 503.35
• InChiKey: OOTOLVPVEJGSFP-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  30.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl ((((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate 在 sodium periodate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 2.25h， 以68%的产率得到1-[(2R,5R)-5-(diethoxyphosphorylmethoxy)-2,5-dihydrofuran-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and P2Y2 receptor agonist activities of uridine 5′-phosphonate analogues

  摘要：

  We explored the influence of modifications of uridine 5'-methylenephosphonate on biological activity at the human P2Y(2) receptor. Key steps in the synthesis of a series of 5-substituted uridine 5'-methylenephosphonates were the reaction of a suitably protected uridine 5'-aldehyde with [(diethoxyphosphinyl) methylidene] triphenylphosphorane, C-5 bromination and a Suzuki-Miyaura coupling. These analogues behaved as selective agonists at the P2Y(2) receptor, with three analogues exhibiting potencies in the submicromolar range. Although maximal activities observed with the phosphonate analogues were much less than observed with UTP, high concentrations of the phosphonates had no effect on the stimulatory effect of UTP. These results suggest that these phosphonates bind to an allosteric site of the P2Y(2) receptor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.012
• 作为产物：
  描述：

  苯基氯化硒 、 羟甲基膦酸二乙酯 、 1-(2,3-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以35%的产率得到diethyl ((((2R,3S,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-(phenylselanyl)tetrahydrofuran-2-yl)oxy)methyl)phosphonate
  参考文献：
  名称：

  Synthesis and P2Y2 receptor agonist activities of uridine 5′-phosphonate analogues

  摘要：

  We explored the influence of modifications of uridine 5'-methylenephosphonate on biological activity at the human P2Y(2) receptor. Key steps in the synthesis of a series of 5-substituted uridine 5'-methylenephosphonates were the reaction of a suitably protected uridine 5'-aldehyde with [(diethoxyphosphinyl) methylidene] triphenylphosphorane, C-5 bromination and a Suzuki-Miyaura coupling. These analogues behaved as selective agonists at the P2Y(2) receptor, with three analogues exhibiting potencies in the submicromolar range. Although maximal activities observed with the phosphonate analogues were much less than observed with UTP, high concentrations of the phosphonates had no effect on the stimulatory effect of UTP. These results suggest that these phosphonates bind to an allosteric site of the P2Y(2) receptor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.012