2-methyl-5,6-dihydro-5-oxo-6-β-D-ribofuranosylimidazo<1,2-c>pyrimidine | 90754-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5,6-dihydro-5-oxo-6-β-D-ribofuranosylimidazo<1,2-c>pyrimidine
• 英文别名: 2-methyl-6-β-D-ribofuranosylimiidazo<1,2-c>pyrimidin-5(6H)-one；6-(β-D-ribofuranosyl)-2-methyl-6H-imidazo[1,2-c]pyrimidin-5-one；2-methyl-5,6-dihydro-5-oxo-6-β-D-ribofuranosylimidazo[1,2-c]pyrimidine；6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methyl-imidazo[1,2-c]pyrimidin-5-one；6-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-methylimidazo[1,2-c]pyrimidin-5-one
• CAS: 90754-37-3
• 化学式: C₁₂H₁₅N₃O₅
• 分子量: 281.268
• InChiKey: VJZGVZAFXWSLQT-QCNRFFRDSA-N

物化性质

• 沸点：
  653.5±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-2-methyl-6H-imidazo[1,2-c]pyrimidin-5-one 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 96.0h， 以95%的产率得到2-methyl-5,6-dihydro-5-oxo-6-β-D-ribofuranosylimidazo<1,2-c>pyrimidine
  参考文献：
  名称：

  Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: synthesis and antiviral evaluation

  摘要：

  The preparation of a series of novel 6-(beta-D-ribofuranosyl)-2-alkyl/aryl-6H-imidazo [1,2-c]pyrimidin-5-one nucleosides and the 2-nitrile nucleosides, 6-(beta-D-ribofuranosyl)-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carbonitrile and 2R and 2S isomers of 6-(beta-D-ribofuranosyl)-5-oxo-2,3,5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile, is described using two synthetic approaches. The nucleoside mimetics described were evaluated against a wide range of viral types and strains in cell culture. With the exception of one nucleoside, which displayed anti-CMV activity at toxic concentrations, none of the compounds showed antiviral activity most likely due to a lack of substrate recognition by viral and/or cellular nucleoside kinases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.017

文献信息

• Ring-extended products from the reaction of epoxy carbonyl compounds and nucleic acid bases
  作者：Vasu Nair、Rick J. Offerman

  DOI：10.1021/jo00350a039

  日期：1985.12
• Krzyzosiak, Wlodzimierz J.; Biernat, Jacek; Ciesiolka, Jerzy, Polish Journal of Chemistry, 1983, vol. 57, # 7-9, p. 779 - 787
  作者：Krzyzosiak, Wlodzimierz J.、Biernat, Jacek、Ciesiolka, Jerzy、Gornicki, Piotr、Wiewiorowski, Maciej

  DOI：——

  日期：——
• Novel imidazo[1,2-c]pyrimidine base-modified nucleosides: synthesis and antiviral evaluation
  作者：Nurolaini Kifli、Erik De Clercq、Jan Balzarini、Claire Simons

  DOI：10.1016/j.bmc.2004.05.017

  日期：2004.8.1

  The preparation of a series of novel 6-(beta-D-ribofuranosyl)-2-alkyl/aryl-6H-imidazo [1,2-c]pyrimidin-5-one nucleosides and the 2-nitrile nucleosides, 6-(beta-D-ribofuranosyl)-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carbonitrile and 2R and 2S isomers of 6-(beta-D-ribofuranosyl)-5-oxo-2,3,5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile, is described using two synthetic approaches. The nucleoside mimetics described were evaluated against a wide range of viral types and strains in cell culture. With the exception of one nucleoside, which displayed anti-CMV activity at toxic concentrations, none of the compounds showed antiviral activity most likely due to a lack of substrate recognition by viral and/or cellular nucleoside kinases. (C) 2004 Elsevier Ltd. All rights reserved.