8-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde | 524724-74-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde
• 英文别名: 8-methyl-2-(p-tolyl)imidazo[1,2-a]pyridine-3-carbaldehyde
• CAS: 524724-74-1
• 化学式: C₁₆H₁₄N₂O
• mdl: MFCD03617283
• 分子量: 250.3
• InChiKey: MSWITZHKOCCTNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  8-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde 在 copper(l) iodide 、 sodium azide 、 硫酸 、 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 8-methyl-2-p-tolyl-imidazo[1,2-a]pyridine-3-carbaldehyde-O-[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl oxime
  参考文献：
  名称：

  Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies

  摘要：

  The present article reports the synthesis and anticonvulsant studies of new 2-arylimidazo[1,2-a]pyridines carrying suitably substituted 1,2,3-triazoles as well as their intermediates. The structures of newly synthesized compounds were confirmed by various spectroscopic techniques. The anticonvulsant study was carried out by MES and scPTZ screening methods, while their toxicity study was performed following Rotarod method. The active compounds showed enhanced seizure control in scPTZ method when compared with that of MES method. Compounds 3f, 4c, 4f, 5k, 5p and 5w carrying active pharmacophores exhibited complete protection against seizure and their results were comparable with standard drug diazepam. Majority of new compounds were found to be non-toxic, while few of them showed toxicity at 100 mg/kg. The c log P values of target compounds are in the range of 3.5-5.3, which confirm their lipophilic nature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.086
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 8-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde
  参考文献：
  名称：

  Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies

  摘要：

  The present article reports the synthesis and anticonvulsant studies of new 2-arylimidazo[1,2-a]pyridines carrying suitably substituted 1,2,3-triazoles as well as their intermediates. The structures of newly synthesized compounds were confirmed by various spectroscopic techniques. The anticonvulsant study was carried out by MES and scPTZ screening methods, while their toxicity study was performed following Rotarod method. The active compounds showed enhanced seizure control in scPTZ method when compared with that of MES method. Compounds 3f, 4c, 4f, 5k, 5p and 5w carrying active pharmacophores exhibited complete protection against seizure and their results were comparable with standard drug diazepam. Majority of new compounds were found to be non-toxic, while few of them showed toxicity at 100 mg/kg. The c log P values of target compounds are in the range of 3.5-5.3, which confirm their lipophilic nature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.086

文献信息

• Visible light induced tetramethylethylenediamine assisted formylation of imidazopyridines
  作者：Golam Kibriya、Avik K. Bagdi、Alakananda Hajra

  DOI：10.1039/c8ob00532j

  日期：——

  A metal-free visible light induced C-3 formylation of imidazo[1,2-a]pyridine has been developed using tetramethylethylenediamine (TMEDA) as a one carbon source. An array of 3-formyl imidazo[1,2-a]pyridines with wide functionality are synthesized using rose bengal as a photosensitizer under ambient air.

  使用四甲基乙二胺（TMEDA）作为一种碳源，开发了一种无金属的可见光诱导的咪唑并[1,2- a ]吡啶的C-3甲酰化反应。在环境空气下，使用玫瑰红作为光敏剂，合成了具有广泛功能的3-甲酰基咪唑并[1,2- a ]吡啶。
• Design, Synthesis and Biological Evaluation of Imidazo[1,2-a]pyridine Derivatives as Novel DPP-4 Inhibitors
  作者：Qing Li、Muxing Zhou、Li Han、Qing Cao、Xinning Wang、LeiLei Zhao、Jinpei Zhou、Huibin Zhang

  DOI：10.1111/cbdd.12560

  日期：2015.10

  A new series of DPP‐4 inhibitors with imidazo[1,2‐a]pyridine scaffold were designed by exploiting scaffold hopping strategy and docking study. Based on docking binding model, structural modifications of 2‐benzene ring and pyridine moieties of compound 5a led to the identification of compound 5d with 2, 4‐dichlorophenyl group at the 2‐position as a potent (IC50 = 0.13 μm), selective (DPP‐8/DPP‐4 = 215 and DPP‐9/DPP‐4 = 192) and in vivo efficacious DPP‐4 inhibitor. Further, molecular docking revealed that compound 5d could retain key binding features of DPP‐4 with the pyridine moiety of imidazo[1,2‐a]pyridine ring providing an additional π−π interaction with Phe357 of DPP‐4. Compound 5d might be a promising lead for further development of novel DPP‐4 inhibitor treating T2DM.