6-benzyloxy-7-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine | 579486-44-5

• 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: 6-benzyloxy-7-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine
• 英文别名: 7-(5-methoxypentyl)-6-benzyloxy-2-chloro-3-deazapurine
• CAS: 579486-44-5
• 化学式: C₁₉H₂₂ClN₃O₂
• 分子量: 359.856
• InChiKey: XQPRAGADUYVAPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.17
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-benzyloxy-7-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine 、 3-乙基-4-甲基苯胺 反应 24.0h， 以59%的产率得到2-(3-ethyl-4-methylanilino)-7-(5-methoxypentyl)-6-oxo-3-deazapurine
  参考文献：
  名称：

  7-Alkyl-N2-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity

  摘要：

  Several 2-anilino- and 2-benzylamino-3-deaza-6-oxopurines [3-deazaguanines] and selected 8-methyl and 8-aza analogs have been synthesized. 7-Substituted N-2-(3-ethyl-4-methylphenyl)-3-deazaguanines were potent and selective inhibitors of Gram+ bacterial DNA polymerase (pol) IIIC, and 7-substituted N-2-(3,4-dichlorobenzyl)-3-deazaguanines were potent inhibitors of both pol IIIC and pol IIIE from Gram+ bacteria, but weakly inhibited pol IIIE from Gram- bacteria. Potent enzyme inhibitors in both classes inhibited the growth of Gram+ bacteria (MICs 2.5-10 mu g/ml), and were inactive against the Gram- organism Escherichia coli. Several derivatives had moderate protective activity in Staphylococcus aureus-infected mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.093
• 作为产物：
  描述：

  4,6-二氯-1H-咪唑并[4,5-c]吡啶 在 sodium 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 6-benzyloxy-7-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine 、 6-benzyloxy-9-(5-methoxypentyl)-4-chloroimidazo[4,5-c]pyridine
  参考文献：
  名称：

  7-Alkyl-N2-substituted-3-deazaguanines. Synthesis, DNA polymerase III inhibition and antibacterial activity

  摘要：

  Several 2-anilino- and 2-benzylamino-3-deaza-6-oxopurines [3-deazaguanines] and selected 8-methyl and 8-aza analogs have been synthesized. 7-Substituted N-2-(3-ethyl-4-methylphenyl)-3-deazaguanines were potent and selective inhibitors of Gram+ bacterial DNA polymerase (pol) IIIC, and 7-substituted N-2-(3,4-dichlorobenzyl)-3-deazaguanines were potent inhibitors of both pol IIIC and pol IIIE from Gram+ bacteria, but weakly inhibited pol IIIE from Gram- bacteria. Potent enzyme inhibitors in both classes inhibited the growth of Gram+ bacteria (MICs 2.5-10 mu g/ml), and were inactive against the Gram- organism Escherichia coli. Several derivatives had moderate protective activity in Staphylococcus aureus-infected mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.093