2-benzenesulfonylmethyl-6-bromo-3-nitro-imidazo[1,2-a]pyridine

• 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: 2-benzenesulfonylmethyl-6-bromo-3-nitro-imidazo[1,2-a]pyridine
• 英文别名: 6-bromo-3-nitro-2-phenylsulfonylmethylimidazo[1,2-a]pyridine；2-(Benzenesulfonylmethyl)-6-bromo-3-nitroimidazo[1,2-a]pyridine；2-(benzenesulfonylmethyl)-6-bromo-3-nitroimidazo[1,2-a]pyridine
• 化学式: C₁₄H₁₀BrN₃O₄S
• 分子量: 396.221
• InChiKey: BLSSKXJKINWGFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzenesulfonylmethyl-6-bromo-3-nitro-imidazo[1,2-a]pyridine 、 2-萘硼酸 在 四(三苯基膦)钯 、 四丁基溴化铵 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以78%的产率得到6-naphthalen-2-yl-3-nitro-2-phenylsulfonylmethylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  咪唑并[1,2- a ]吡啶在水介质中的微波辅助铃木交叉偶联反应

  摘要：

  在没有有机助溶剂的情况下，在含水介质中使用微波辐射，通过铃木交叉偶联反应，描述了一种新的简单，快速，高产率的合成各种6-芳基-2-芳基磺酰基甲基-3-硝基咪唑并[1,2- a ]吡啶的方法。存在四丁基溴化铵。

  DOI：

  10.1016/j.tetlet.2006.07.098
• 作为产物：
  描述：

  6-溴-2-(氯甲基)咪唑并[1,2-a]吡啶 在 硫酸 、 硝酸 、 碳酸氢钠 、 sodium sulfite 作用下， 以 水 为溶剂， 生成 2-benzenesulfonylmethyl-6-bromo-3-nitro-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Targeting the human parasite Leishmania donovani: Discovery of a new promising anti-infectious pharmacophore in 3-nitroimidazo[1,2-a]pyridine series

  摘要：

  We report herein the discovery of antileishmanial molecules based on the imidazo[1,2-a]pyridine ring. In vitro screenings of imidazopyridines belonging to our chemical library, toward the promastigotes stage of Leishmania donovani, J774A. 1 murine and HepG2 human cells, permitted to identify three selective hit-compounds (12, 20 and 28). New derivatives were then synthesized to allow structure-activity and -toxicity relationships analyses, enabling to characterize a lead-compound (44) displaying both a high potency (IC50 = 1.8 mu M) and a good selectivity index, in comparison with three antileishmanial reference drug-compounds (amphotericin B, miltefosine and pentamidine). Moreover, lead-compound 44 also exhibits good in vitro activity against the intracellular amastigote stage of L. donovani. Thus, the 6-halo-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridine scaffold appears as a new promising selective antileishmanial pharmacophore, especially when substituted at position 8 by a bromine atom. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.002

文献信息

• An efficient microwave-assisted Suzuki cross-coupling reaction of imidazo[1,2-a]pyridines in aqueous medium
  作者：Maxime D. Crozet、Caroline Castera-Ducros、Patrice Vanelle

  DOI：10.1016/j.tetlet.2006.07.098

  日期：2006.9

  A new simple, rapid and high yielding synthesis of various 6-aryl-2-arylsulfonylmethyl-3-nitroimidazo[1,2-a]pyridines by Suzuki cross-coupling reaction is described using microwave irradiation in aqueous medium without organic co-solvent in the presence of tetrabutylammonium bromide.

  在没有有机助溶剂的情况下，在含水介质中使用微波辐射，通过铃木交叉偶联反应，描述了一种新的简单，快速，高产率的合成各种6-芳基-2-芳基磺酰基甲基-3-硝基咪唑并[1,2- a ]吡啶的方法。存在四丁基溴化铵。
• An Efficient Synthetic Route to New Imidazo[1,2-a]pyridines by Cross-Coupling Reactions in Aqueous Medium
  作者：Patrice Vanelle、Caroline Castera、Maxime D. Crozet

  DOI：10.3987/com-05-10548

  日期：——
• Targeting the human parasite Leishmania donovani: Discovery of a new promising anti-infectious pharmacophore in 3-nitroimidazo[1,2-a]pyridine series
  作者：Caroline Castera-Ducros、Lucie Paloque、Pierre Verhaeghe、Magali Casanova、Christophe Cantelli、Sébastien Hutter、Floriane Tanguy、Michèle Laget、Vincent Remusat、Anita Cohen、Maxime D. Crozet、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.bmc.2013.09.002

  日期：2013.11

  We report herein the discovery of antileishmanial molecules based on the imidazo[1,2-a]pyridine ring. In vitro screenings of imidazopyridines belonging to our chemical library, toward the promastigotes stage of Leishmania donovani, J774A. 1 murine and HepG2 human cells, permitted to identify three selective hit-compounds (12, 20 and 28). New derivatives were then synthesized to allow structure-activity and -toxicity relationships analyses, enabling to characterize a lead-compound (44) displaying both a high potency (IC50 = 1.8 mu M) and a good selectivity index, in comparison with three antileishmanial reference drug-compounds (amphotericin B, miltefosine and pentamidine). Moreover, lead-compound 44 also exhibits good in vitro activity against the intracellular amastigote stage of L. donovani. Thus, the 6-halo-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridine scaffold appears as a new promising selective antileishmanial pharmacophore, especially when substituted at position 8 by a bromine atom. (C) 2013 Elsevier Ltd. All rights reserved.