3-benzyl-3H-imidazo[4,5-b]pyridine 4-oxide | 1137089-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-benzyl-3H-imidazo[4,5-b]pyridine 4-oxide
• CAS: 1137089-67-8
• 化学式: C₁₃H₁₁N₃O
• 分子量: 225.25
• InChiKey: BWYPKIYKIPNRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-benzyl-3H-imidazo[4,5-b]pyridine 4-oxide 在 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以70%的产率得到3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine
  参考文献：
  名称：

  Synthesis and modulation properties of imidazo[4,5-b]pyridin-7-one and indazole-4,7-dione derivatives towards the Cryptosporidium parvum CpABC3 transporter

  摘要：

  The syntheses of new N-polysubstituted imidazo[4,5-b]pyridine-7-one (IF, 5 and 8a-8f) and indazole-4,7-dione (ID, 9 and 10) derivatives are described. The binding affinity of IP and ID towards the recombinant Nucleotide Binding Domain NBD1 of Cryptosporidium parvum CpABC3 was evaluated by intrinsic fluorescence quenching. IP induced a moderate quenching of the intrinsic fluorescence of H6-NBD1 whereas IDs 9 and 10 showed a binding affinity comparable to the ATP analogue TNP-ATP. In addition, 8d, Se and 10 were shown to be competitive inhibitors of the ATPase activity, but with low affinity. These compounds could thus act like some flavonoid derivatives, which can partly overlap both the nucleotide-binding site and the adjacent hydrophobic steroid-binding region of mammalian P-glycoproteins.

  DOI：

  10.1016/j.ejmech.2010.02.033
• 作为产物：
  描述：

  溴甲苯 、 4-hydroxyimidazo[4,5-b]pyridine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以71%的产率得到1-benzyl-1H-imidazo[4,5-b]pyridine 4-oxide
  参考文献：
  名称：

  Regioselective N-alkylation of imidazo[4,5-b]pyridine-4-oxide derivatives: an experimental and DFT study

  摘要：

  Regioselectivities were determined for N-alkylations of imidazo[4,5-bipyridine-4-oxide and 2-methyl-imidazo[4,5-b]pyridme-4-oxide with benzyl bromide or benzyl iodide at RT using K2CO3 in DMF as a base. Experimental attempts have shown that N-1/N-3 ratios slightly varied according to the Substitution on C-2 position. This was confirmed by DFT calculations in solvent phase. This computational study has shown first that this N-benzylation reaction passed through a S(N)2 mechanism. Moreover, regioselectivity of N-benzylation has appeared essentially governed by 'steric approach control'. It explained that opposite N-1/N-3 ratios were obtained with imidazo[4,5-b]pyridine-4-oxide and its 2-methyl-substituted analog. Finally, regioselectivities slightly varied with the nature of benzyl halide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.006