2-(2-chlorophenyl)-N-cyclohexyl-5-methoxyimidazo[1,2-a]pyridin-3-amine | 1316721-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-chlorophenyl)-N-cyclohexyl-5-methoxyimidazo[1,2-a]pyridin-3-amine
• CAS: 1316721-58-0
• 化学式: C₂₀H₂₂ClN₃O
• 分子量: 355.867
• InChiKey: HQYQWGLBZYNWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  38.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-bromo-2-(2-chlorophenyl)-N-cyclohexylimidazo[1,2-a]pyridin-3-amine 、 sodium methylate 反应 4.0h， 以98%的产率得到2-(2-chlorophenyl)-N-cyclohexyl-5-methoxyimidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  During random screening of a small in-house library of compounds, certain substituted imidazo[1,2-a]pyridines were found to be weak allosteric inhibitors of HIV-1 reverse transcriptase (RT). A library of these compounds was prepared using the Groebke reaction and a subset of compounds prepared from 2-chlorobenzaldehyde, cyclohexyl isocyanide and a 6-substituted 2-aminopyridine showed good inhibitory activity in enzymatic (RT) and HIV anti-infectivity MAGI whole cell assays. The compound showing the best anti-HIV-1 IIIB whole cell activity (MAGI IC(50) = 0.18 mu M, IC(90) = 1.06 mu M), along with a good selectivity index (>800), was 2-(2-chlorophenyl)-3-(cyclohexylamino) imidazo[1,2-a]pyridine-5-carbonitrile 38. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.062

文献信息

• Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Moira L. Bode、David Gravestock、Simon S. Moleele、Christiaan W. van der Westhuyzen、Stephen C. Pelly、Paul A. Steenkamp、Heinrich C. Hoppe、Tasmiyah Khan、Lindiwe A. Nkabinde

  DOI：10.1016/j.bmc.2011.05.062

  日期：2011.7

  During random screening of a small in-house library of compounds, certain substituted imidazo[1,2-a]pyridines were found to be weak allosteric inhibitors of HIV-1 reverse transcriptase (RT). A library of these compounds was prepared using the Groebke reaction and a subset of compounds prepared from 2-chlorobenzaldehyde, cyclohexyl isocyanide and a 6-substituted 2-aminopyridine showed good inhibitory activity in enzymatic (RT) and HIV anti-infectivity MAGI whole cell assays. The compound showing the best anti-HIV-1 IIIB whole cell activity (MAGI IC(50) = 0.18 mu M, IC(90) = 1.06 mu M), along with a good selectivity index (>800), was 2-(2-chlorophenyl)-3-(cyclohexylamino) imidazo[1,2-a]pyridine-5-carbonitrile 38. (C) 2011 Elsevier Ltd. All rights reserved.