6-溴-N-叔丁基-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-胺 | 1001736-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6-溴-N-叔丁基-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-胺
• 英文名称: 6-bromo-N-tert-butyl-2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine
• CAS: 1001736-32-8
• 化学式: C₁₇H₁₇BrClN₃
• mdl: MFCD19715617
• 分子量: 378.699
• InChiKey: PFRRUARYDXEQGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-N-叔丁基-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-胺 、 4-氯苯硼酸 在 四(三苯基膦)钯 、 四丁基溴化铵 、 sodium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 3.0h， 以302 mg的产率得到N-tert-butyl-2,6-di-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors

  摘要：

  A study of structure-based modulation of known ligands of hTopoII alpha, an important enzyme involved in DNA processes, coupled with synthesis and in vitro assays led to the establishment of a strategy of rational switch in mode of inhibition of the enzyme's catalytic cycle. 6-Arylated derivatives of known imidazopyridine ligands were found to be selective inhibitors of hTopoII alpha, while not showing TopoI inhibition and DNA binding. Interestingly, while the parent imidazopyridines acted as ATP-competitive inhibitors, arylated derivatives inhibited DNA cleavage similar to merbarone, indicating a switch in mode of inhibition from ATP-hydrolysis to the DNA-cleavage stage of catalytic cycle of the enzyme. The 6-aryl-imidazopyridines were relatively more cytotoxic than etoposide in cancer cells and less toxic to normal cells. Such unprecedented strategy will encourage research on "choice-based change" in target-specific mode of action for rapid drug discovery.

  DOI：

  10.1021/acsmedchemlett.5b00040
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 、 异氰酸叔丁酯 、 4-氯苯甲醛 在 氯化锆(IV) 作用下， 以 PEG-400 为溶剂， 反应 0.12h， 以82%的产率得到6-溴-N-叔丁基-2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-胺
  参考文献：
  名称：

  多功能N融合氨基咪唑的高度灵活高效的Ugi型多组分合成

  摘要：

  研究了微波促进的高柔性，高效的Ugi型杂环multi与氯化锆（IV）催化的醛和异氰酸酯的多组分反应。该通用方案以极高的收率提供了非常重要的医学上重要的，用途广泛的N融合氨基咪唑库的可靠合成。在较早描述的方法中作为麻烦的反应物遭受的反应性差的杂环am，功能和空间受阻的醛在该方法中被认为是可行的底物。发现ZrCl 4的有效催化以及微波辐照的作用对于获得方案的优异灵活性和效率至关重要。 多组分反应-N-杂环-催化-氯化锆-微波

  DOI：

  10.1055/s-0029-1216916

文献信息

• Catalytic activity of aqueous cationic polyurethane dispersions: A novel feature of polyurethanes
  作者：Hamed Daemi、Reza Rezaieyeh Rad、Mehdi Barikani、Mehdi Adib

  DOI：10.1016/j.apcata.2013.08.023

  日期：2013.11

  Polyurethane ionomers are well-known and user-friendly polymers. Here, we introduce their catalytic activity for organic reactions as a novel aspect of these polymers. We selected an isocyanide-based multicomponent reaction for proving the catalytic activity of polyurethane ionomers. Therefore, a convenient and very mild methodology is described for the preparation of 3-aminoimidazo[1,2-a]pyridines via a three component reaction between 2-aminopyridines, aldehydes and isocyanides in the presence of a cationic polyurethane dispersion at low reaction temperatures, in short reaction times and excellent yields. (C) 2013 Elsevier B.V. All rights reserved.
• One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides
  作者：Mehdi Adib、Ehsan Sheikhi、Narjes Rezaei

  DOI：10.1016/j.tetlet.2011.04.002

  日期：2011.6

  A one-pot synthesis of imidazo[1,2-a]pyridines is described. Benzyl halides or benzyl tosylates are oxidized to aldehydes under mild Kornblum conditions which then undergo a three-component reaction with various 2-aminopyridines and isocyanides to afford the imidazo[1,2-a]pyridines in excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.