benzyl-[6-bromo-2-(2,5-dimethoxy-phenyl)-imidazo[1,2-a]pyridin-3-yl]-amine | 1022702-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl-[6-bromo-2-(2,5-dimethoxy-phenyl)-imidazo[1,2-a]pyridin-3-yl]-amine
• 英文别名: N-benzyl-6-bromo-2-(2,5-dimethoxyphenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 1022702-55-1
• 化学式: C₂₂H₂₀BrN₃O₂
• 分子量: 438.324
• InChiKey: XYIFDPBEKWRUEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 苄异腈 、 2,5-二甲氧基苯甲醛 在 montmorillonite clay K₁₀ 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以67%的产率得到benzyl-[6-bromo-2-(2,5-dimethoxy-phenyl)-imidazo[1,2-a]pyridin-3-yl]-amine
  参考文献：
  名称：

  6-Substituted imidazo[1,2-a]pyridines: Synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2

  摘要：

  A range of 6-substituted imidazo[1,2-a]pyridines were synthesized using a multicomponent coupling reaction. Most of these compounds were found to exhibit excellent activity against the colon cancer cell lines HT-29 and Caco-2, whilst not showing significant toxicity against white blood cells. Our studies have shown that the proteolytic phase of apoptosis was initiated 2 h after treatment with these imidazo [1,2-a]pyridines. The data suggests that the imidazo[1,2-a]pyridine-induced cell death in HT-29 and Caco-2 cells is mediated via pathway(s) that include the release of cytochrome c from the mitochondria to the cytosol and the activation of caspase 3 and caspase 8. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.036

文献信息

• IMIDAZO[1,2 A] PYRIDINE 6 CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE
  申请人：Farkas (Nee Dahan) Nurit Esperance

  公开号：US20120101122A1

  公开（公告）日：2012-04-26

  This invention relates to the manufacture of novel chemical compounds which have biological activity, particularly to novel chemical compounds that are cytotoxic against colon cancer cells and colon cancer cell lines. The manufacturing of said chemical compounds displaying anti-cancer properties employs the use of multi-component chemical reactions. The object of this invention is to manufacture and isolate analogues of imidazo[1,2-a]pyridine, namely compounds of Formula 1, which are cytotoxic against colon cancer cells, while concomitantly being relatively inactive against white blood cells. wherein, R is bromo, methyl, phenyl, nitro, hydrogen or an amide functional group; R 1 is benzyl, 2,6-dimethylphenyl or cyclohexyl; and R 2 is methoxy, benzyloxy or hydroxy.
• US8481740B2
  申请人：——

  公开号：US8481740B2

  公开（公告）日：2013-07-09
• 6-Substituted imidazo[1,2-a]pyridines: Synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2
  作者：Nurit Dahan-Farkas、Candice Langley、Amanda L. Rousseau、Dharmendra B. Yadav、Hajierah Davids、Charles B. de Koning

  DOI：10.1016/j.ejmech.2011.07.036

  日期：2011.9

  A range of 6-substituted imidazo[1,2-a]pyridines were synthesized using a multicomponent coupling reaction. Most of these compounds were found to exhibit excellent activity against the colon cancer cell lines HT-29 and Caco-2, whilst not showing significant toxicity against white blood cells. Our studies have shown that the proteolytic phase of apoptosis was initiated 2 h after treatment with these imidazo [1,2-a]pyridines. The data suggests that the imidazo[1,2-a]pyridine-induced cell death in HT-29 and Caco-2 cells is mediated via pathway(s) that include the release of cytochrome c from the mitochondria to the cytosol and the activation of caspase 3 and caspase 8. (C) 2011 Elsevier Masson SAS. All rights reserved.