1-(2,3-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione | 74831-43-9

• 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: 1-(2,3-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2R)-2,3-dihydrofuran-2-yl]pyrimidine-2,4-dione
• CAS: 74831-43-9；37076-63-4
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: DDUYFJSFLJDOJK-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione 在 sodium periodate 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.25h， 生成 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：

  1,2-dideoxy-1β-(1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)-D-ribofuranuronic acid 在 N,N-二甲基甲酰胺二新戊基乙缩醛 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到1-(2,3-dihydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates

  摘要：

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.038

文献信息

• Synthesis and P2Y2 receptor agonist activities of uridine 5′-phosphonate analogues
  作者：Sara Van Poecke、Matthew O. Barrett、T. Santhosh Kumar、Davy Sinnaeve、José C. Martins、Kenneth A. Jacobson、T. Kendall Harden、Serge Van Calenbergh

  DOI：10.1016/j.bmc.2012.02.012

  日期：2012.4

  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.
• Synthesis, anti-HIV activity, and resistance profiles of ribose modified nucleoside phosphonates
  作者：Richard L. Mackman、Constantine G. Boojamra、Vidya Prasad、Lijun Zhang、Kuei-Ying Lin、Oleg Petrakovsky、Darius Babusis、James Chen、Janet Douglas、Deborah Grant、Hon C. Hui、Choung U. Kim、David Y. Markevitch、Jennifer Vela、Adrian Ray、Tomas Cihlar

  DOI：10.1016/j.bmcl.2007.10.038

  日期：2007.12

  A series of nucleoside phosphonate reverse transcriptase (RT) inhibitors have been synthesized and their anti-HIV activity and resistance profiles evaluated. The most potent analog [5-(6-amino-purin-9-yl)-2,5-dihydro-furan-2-yloxymethyl]-phosphonic acid (d4AP) demonstrated a HIV EC50 = 2.1 mu M, and the most favorable resistance profile against HIV-1 variants with K65R, M184V or multiple thymidine analog mutations in RT. (c) 2007 Elsevier Ltd. All rights reserved.