2-phenylsulfonylmethylimidazo[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-phenylsulfonylmethylimidazo[1,2-a]pyridine
• 英文别名: 2-(Benzenesulfonylmethyl)imidazo[1,2-a]pyridine
• 化学式: C₁₄H₁₂N₂O₂S
• 分子量: 272.327
• InChiKey: PPSICRYRUFXDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 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：
  59.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 在 碳酸氢钠 、 sodium sulfite 作用下， 以 乙醇 、 水 为溶剂， 78.0~120.0 ℃ 、500.01 kPa 条件下， 反应 1.0h， 生成 2-phenylsulfonylmethylimidazo[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

• 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.