7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine | 287101-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[7-(2-phenylethynyl)imidazo[4,5-b]pyridin-3-yl]oxolan-2-yl]methyl acetate
• CAS: 287101-38-6
• 化学式: C₂₅H₂₃N₃O₇
• 分子量: 477.474
• InChiKey: BYAGBXXFMVHMOF-HBAHCVPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine 在 盐酸 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 18.0h， 生成 7-phenylethynylimidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Cytokinin Activity of Fluorescent 7-Phenylethynylimidazo[4,5-b]pyridine and Its Riboside

  摘要：

  7-Phenylethynylimidazo[4,5-b]pyridine and its riboside have been newly developed as fluorescent carbon-substituted cytokinin analogues. Palladium-catalyzed coupling of 7-iodo-3-(tri-O-acetyl-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine with phenylacetylene followed by ammonolysis afforded the 7-phenylethynyl riboside via its tri-O-acetate. Acid hydrolysis of the riboside provided its free base, which showed a marked enhancement in fluorescence intensity in an aqueous alkaline solution. The free base and its riboside were more active than the corresponding 6-phenylethynylpurine and its riboside, respectively, in Amaranthus betacyanin and tobacco callus bioassays. Surprisingly, the imidazo[4,5-b]pyridine base exhibited strong cytokinin activity comparable to that of NG-benzyladenine in the tobacco callus bioassay. This compound would be useful for studying localization and transport of cytokinins in cells or tissues of plants.

  DOI：

  10.1021/jf0000225
• 作为产物：
  描述：

  7-amino-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-b]pyridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二碘甲烷 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 7-phenylethynyl-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis and Cytokinin Activity of Fluorescent 7-Phenylethynylimidazo[4,5-b]pyridine and Its Riboside

  摘要：

  7-Phenylethynylimidazo[4,5-b]pyridine and its riboside have been newly developed as fluorescent carbon-substituted cytokinin analogues. Palladium-catalyzed coupling of 7-iodo-3-(tri-O-acetyl-beta-D-ribofuranosyl)imidazo[4,5-b]pyridine with phenylacetylene followed by ammonolysis afforded the 7-phenylethynyl riboside via its tri-O-acetate. Acid hydrolysis of the riboside provided its free base, which showed a marked enhancement in fluorescence intensity in an aqueous alkaline solution. The free base and its riboside were more active than the corresponding 6-phenylethynylpurine and its riboside, respectively, in Amaranthus betacyanin and tobacco callus bioassays. Surprisingly, the imidazo[4,5-b]pyridine base exhibited strong cytokinin activity comparable to that of NG-benzyladenine in the tobacco callus bioassay. This compound would be useful for studying localization and transport of cytokinins in cells or tissues of plants.

  DOI：

  10.1021/jf0000225