3-cyano-5-β-D-arabinofuranosylpyridine | 156686-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-cyano-5-β-D-arabinofuranosylpyridine
• 英文别名: 5-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyridine-3-carbonitrile；5-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-3-carbonitrile
• CAS: 156686-53-2
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: SAAMGCIISNTKNO-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-cyano-5-β-D-arabinofuranosylpyridine 在 硫化氢 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到3-thiocarbamoyl-5-β-D-arabinofuranosylpyridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides

  摘要：

  The addition reaction of either 3-bromo-5-lithiopyridine (2a) or 3-cyano-5-lithiopyridine (2b) to 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (1) or 2,4:3,5-di-O-benzylidene-aldehydo-D-lyxose (8) gave respectively a D-gluco/D-manno mixture of 3-bromo- and 3-cyano-5-(2,3:4,5-di-O-isopropylidene-pentitol-1-yl)pyridine (3a,b) or a D-galacto/D-talo mixture of respectively 3-bromo- and 3-cyano-5-(2,4:3,5-di-O-benzylidene-pentitol-1-yl)pyridine (9a,b). Mesylation of C-1' followed by reaction with CF3COOH/H2O resulted in the formation of the corresponding D-arabino- or D-lyxofuranosyl pyridine C-nucleosides. The cyano group of (5b) and (11b) was converted into a carbamoyl group using Amberlite IRA 400 (OH-). 3-Cyano-5-D-arabinofuranosylpyridine (5b) was converted into 3-thiocarbamoyl-5-D-arabinofuranosylpyridine (7) using H2S and triethylamine.None of the test compounds showed a marked cytostatic or antiviral activity in vitro.

  DOI：

  10.1080/15257779408013259
• 作为产物：
  描述：

  2,3-二氟-6-硝基苯胺 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， 反应 7.25h， 生成 3-cyano-5-β-D-arabinofuranosylpyridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides

  摘要：

  The addition reaction of either 3-bromo-5-lithiopyridine (2a) or 3-cyano-5-lithiopyridine (2b) to 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (1) or 2,4:3,5-di-O-benzylidene-aldehydo-D-lyxose (8) gave respectively a D-gluco/D-manno mixture of 3-bromo- and 3-cyano-5-(2,3:4,5-di-O-isopropylidene-pentitol-1-yl)pyridine (3a,b) or a D-galacto/D-talo mixture of respectively 3-bromo- and 3-cyano-5-(2,4:3,5-di-O-benzylidene-pentitol-1-yl)pyridine (9a,b). Mesylation of C-1' followed by reaction with CF3COOH/H2O resulted in the formation of the corresponding D-arabino- or D-lyxofuranosyl pyridine C-nucleosides. The cyano group of (5b) and (11b) was converted into a carbamoyl group using Amberlite IRA 400 (OH-). 3-Cyano-5-D-arabinofuranosylpyridine (5b) was converted into 3-thiocarbamoyl-5-D-arabinofuranosylpyridine (7) using H2S and triethylamine.None of the test compounds showed a marked cytostatic or antiviral activity in vitro.

  DOI：

  10.1080/15257779408013259

文献信息

• Synthesis and Biological Evaluation of Some D-Arabino- and D-Lyxofuranosyl-Pyridine C-Nucleosides
  作者：F. Verberckmoes、E. L. Esmans、J. Balzarini、E. De Clercq

  DOI：10.1080/15257779408013259

  日期：1994.3

  The addition reaction of either 3-bromo-5-lithiopyridine (2a) or 3-cyano-5-lithiopyridine (2b) to 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (1) or 2,4:3,5-di-O-benzylidene-aldehydo-D-lyxose (8) gave respectively a D-gluco/D-manno mixture of 3-bromo- and 3-cyano-5-(2,3:4,5-di-O-isopropylidene-pentitol-1-yl)pyridine (3a,b) or a D-galacto/D-talo mixture of respectively 3-bromo- and 3-cyano-5-(2,4:3,5-di-O-benzylidene-pentitol-1-yl)pyridine (9a,b). Mesylation of C-1' followed by reaction with CF3COOH/H2O resulted in the formation of the corresponding D-arabino- or D-lyxofuranosyl pyridine C-nucleosides. The cyano group of (5b) and (11b) was converted into a carbamoyl group using Amberlite IRA 400 (OH-). 3-Cyano-5-D-arabinofuranosylpyridine (5b) was converted into 3-thiocarbamoyl-5-D-arabinofuranosylpyridine (7) using H2S and triethylamine.None of the test compounds showed a marked cytostatic or antiviral activity in vitro.