2-benzenesulfonylmethyl-6-chloroimidazo[1,2-a]pyridine | 478394-28-4

• 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-chloroimidazo[1,2-a]pyridine
• 英文别名: 2-(Benzenesulfonylmethyl)-6-chloroimidazo[1,2-a]pyridine；2-(benzenesulfonylmethyl)-6-chloroimidazo[1,2-a]pyridine
• CAS: 478394-28-4
• 化学式: C₁₄H₁₁ClN₂O₂S
• 分子量: 306.773
• InChiKey: CFAYJNAIRTYKBR-UHFFFAOYSA-N

物化性质

• 熔点：
  178.7 °C(Solv: isopropanol (67-63-0))
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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

• 作为反应物：
  描述：

  2-benzenesulfonylmethyl-6-chloroimidazo[1,2-a]pyridine 在 jones reagent 、 dimsyl lithium 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 19.0h， 生成 3-benzenesulfonyl-3-(6-chloroimidazo[1,2-a]pyridin-2-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  以苯亚磺酸钠为无痕连接剂，固相合成咪唑并[1,2-a]吡啶。

  摘要：

  描述了在固体载体上的咪唑并[1,2-a]吡啶衍生物的第一个文库的制备。在合成中采用了砜接头策略。固相合成过程中涉及的关键步骤包括（i）通过亚磺酸盐->砜烷基化形成α-卤代酮树脂，（ii）通过用2-氨基吡啶处理形成咪唑并[1,2-a]吡啶环，（iii ）砜阴离子烷基化，以及（iv）通过氧化消除释放无痕产物。合成了12个咪唑并[1,2-a]吡啶的文库。

  DOI：

  10.1021/ol026797b
• 作为产物：
  描述：

  2-氨基-5-氯吡啶 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-benzenesulfonylmethyl-6-chloroimidazo[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.
• Solid-Phase Synthesis of Imidazo[1,2-a]pyridine Using Sodium Benzenesulfinate as a Traceless Linker
  作者：Yu Chen、Yulin Lam、Yee-Hing Lai

  DOI：10.1021/ol026797b

  日期：2002.10.1

  [formula: see text] The preparation of the first library of imidazo[1,2-a]pyridine derivatives on a solid support is described. A sulfone linker strategy was applied in the synthesis. Key steps involved in the solid-phase synthetic procedure include (i) alpha-haloketone resin formation by sulfinate-->sulfone alkylation, (ii) imidazo[1,2-a]pyridine ring formation by treatment with 2-aminopyridine, (iii)

  描述了在固体载体上的咪唑并[1,2-a]吡啶衍生物的第一个文库的制备。在合成中采用了砜接头策略。固相合成过程中涉及的关键步骤包括（i）通过亚磺酸盐->砜烷基化形成α-卤代酮树脂，（ii）通过用2-氨基吡啶处理形成咪唑并[1,2-a]吡啶环，（iii ）砜阴离子烷基化，以及（iv）通过氧化消除释放无痕产物。合成了12个咪唑并[1,2-a]吡啶的文库。