4-[3-(2,6-dimethyl-phenylamino)-6-nitroimidazo[1,2-a]pyridin-2-yl]-benzene-1,3-diol | 1251607-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3-(2,6-dimethyl-phenylamino)-6-nitroimidazo[1,2-a]pyridin-2-yl]-benzene-1,3-diol
• 英文别名: 4-[3-(2,6-Dimethylanilino)-6-nitroimidazo[1,2-a]pyridin-2-yl]benzene-1,3-diol
• CAS: 1251607-04-1
• 化学式: C₂₁H₁₈N₄O₄
• 分子量: 390.398
• InChiKey: GHTFRLHOFPAVIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-5-硝基吡啶 、 2,6-二甲基苯基异腈 、 2,4-二羟基苯甲醛 在 Montmorillonite clay K₁₀ 作用下， 生成 4-[3-(2,6-dimethyl-phenylamino)-6-nitroimidazo[1,2-a]pyridin-2-yl]-benzene-1,3-diol
  参考文献：
  名称：

  [EN] IMIDAZ0[1,2-A] PYRIDINE-6-CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE
  [FR] DÉRIVÉS D'IMIDAZO[1,2-A] PYRIDINE-6-CARBOXAMIDES, LEUR UTILISATION POUR LE TRAITEMENT DU CANCER DU CÔLON ET LEUR PROCÉDÉ DE FABRICATION

  摘要：

  本发明涉及制造具有生物活性的新型化合物，特别是针对结肠癌细胞和结肠癌细胞系具有细胞毒性的新型化合物。制造具有抗癌性质的化合物采用多组分化学反应。本发明的目的是制造和分离咪唑[1,2-a]吡啶的类似物，即公式1的化合物，这些化合物对结肠癌细胞具有细胞毒性，同时对白细胞相对不活性。公式1中，R是溴、甲基、苯基、硝基、氢或酰胺官能团；R1是苄基、2,6-二甲基苯基或环己基；R2是甲氧基、苄氧基或羟基。

  公开号：

  WO2010116302A1

文献信息

• [EN] IMIDAZ0[1,2-A] PYRIDINE-6-CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE<br/>[FR] DÉRIVÉS D'IMIDAZO[1,2-A] PYRIDINE-6-CARBOXAMIDES, LEUR UTILISATION POUR LE TRAITEMENT DU CANCER DU CÔLON ET LEUR PROCÉDÉ DE FABRICATION
  申请人：UNIV WITWATERSRAND JHB

  公开号：WO2010116302A1

  公开（公告）日：2010-10-14

  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. Formula 1 wherein, R is bromo, methyl, phenyl, nitro, hydrogen or an amide functional group; R1 is benzyl, 2,6-dimethylphenyl or cyclohexyl; and R2 is methoxy, benzyloxy or hydroxy.

  本发明涉及制造具有生物活性的新型化合物，特别是针对结肠癌细胞和结肠癌细胞系具有细胞毒性的新型化合物。制造具有抗癌性质的化合物采用多组分化学反应。本发明的目的是制造和分离咪唑[1,2-a]吡啶的类似物，即公式1的化合物，这些化合物对结肠癌细胞具有细胞毒性，同时对白细胞相对不活性。公式1中，R是溴、甲基、苯基、硝基、氢或酰胺官能团；R1是苄基、2,6-二甲基苯基或环己基；R2是甲氧基、苄氧基或羟基。
• IMIDAZO [1,2-A] PYRIDINE-6-CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE
  申请人：University Of Witwatersrand, Johannesburg

  公开号：EP2417136B1

  公开（公告）日：2016-01-06
• 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.