6-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5-oxo-5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile | 750639-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5-oxo-5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile
• 英文别名: 6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]tetrahydrofuran-2-yl]-5-oxo-imidazo[1,2-c]pyrimidine-2-carbonitrile；6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5-oxoimidazo[1,2-c]pyrimidine-2-carbonitrile
• CAS: 750639-34-0
• 化学式: C₃₀H₅₄N₄O₅Si₃
• 分子量: 635.039
• InChiKey: PIZWDQCXGCTXPW-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5-oxo-5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以37%的产率得到2-aminomethyl-6-(2,3-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5-oxo-5,6-tetrahydro-imidazo[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
• 作为产物：
  描述：

  2',3',5'-tri-O-(tert-butyldimethylsilyl)cytidine 在 palladium on activated charcoal N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 6-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)-5-oxo-5,6-tetrahydro-imidazo[1,2-c]pyrimidine-2-carbonitrile
  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

• 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.