8-methyl-2-(4-nitro-phenyl)-imidazo[1,2-a]pyridine | 893-16-3

• 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-nitro-phenyl)-imidazo[1,2-a]pyridine
• 英文别名: 8-Methyl-2-<4-nitro-phenyl>-imidazo<1.2-a>pyridin；2-(4'-Nitrophenyl)-8-methylimidazo[1,2-a]pyridine；8-methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine
• CAS: 893-16-3
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: DSGYGAIWLGBHEG-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methyl-2-(4-nitro-phenyl)-imidazo[1,2-a]pyridine 在 palladium on activated charcoal 2,3-二巯基丁二酸 、 硼烷 、 1-羟基苯并三唑 、 1,3-环己二烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.0h， 生成 [4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-(3-piperidin-1-yl-propyl)-amine
  参考文献：
  名称：

  Novel human histamine H3 receptor antagonists

  摘要：

  High throughput screening, using the recombinant human H-3 receptor, was used to identify novel histamine H-3 receptor antagonists. Evaluation of the lead compounds ultimately afforded potent, selective, orally bioavailable compounds (e.g., 38) with favorable blood-brain barrier penetration. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00738-2
• 作为产物：
  描述：

  2-氨基-3-甲基吡啶 、 2-溴-4'-硝基苯乙酮 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以91 %的产率得到8-methyl-2-(4-nitro-phenyl)-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Beneficial effects of a new neuroprotective compound in neuronal cells and MPTP-administered mouse model of Parkinson's disease

  摘要：

  研究发现，一种带有 8′′-甲基咪唑并吡啶分子的 3,4,5-三甲氧基-N-苯基苯甲酰胺衍生物具有神经保护作用，可防止氧化应激导致的细胞死亡。

  DOI：

  10.1039/d3cc03069e

文献信息

• Phenyl-substituted imidazopyridines
  申请人：Breitenbucher Guy J.

  公开号：US20050085501A1

  公开（公告）日：2005-04-21

  The invention features pharmaceutically-active imidazopyridines and derivatives that are substituted with phenyl, methods of making them, and methods of using them.

  本发明涉及一种具有药理活性的苯基取代的咪唑吡啶及其衍生物，制备方法和使用方法。
• Discovery of novel N-(5-(tert-butyl)isoxazol-3-yl)-N′-phenylurea analogs as potent FLT3 inhibitors and evaluation of their activity against acute myeloid leukemia in vitro and in vivo
  作者：Ying Xu、Ning-Yu Wang、Xue-Jiao Song、Qian Lei、Ting-Hong Ye、Xin-Yu You、Wei-Qiong Zuo、Yong Xia、Li-Dan Zhang、Luo-Ting Yu

  DOI：10.1016/j.bmc.2015.06.033

  日期：2015.8

  FLT3 inhibitors have been explored as a viable therapy for acute myeloid leukemia (AML). However, the clinical outcomes of these FLT3 inhibitors were underwhelming except AC220. Therefore, the development of novel FLT3 inhibitors with high potency against both FLT3-WT and FLT3-ITD mutants are strongly demanded at the present time. In this study, we designed and synthesized a series of novel N-(5-(tert-butyl) isoxazol-3-yl)-N'-phenylurea derivatives as FLT3 inhibitors. SAR studies focused on the fused rings led to the discovery of a series of compounds with high potency against FLT3-ITD-bearing MV4-11 cells and significantly inhibitory activity toward FLT3. Among these compounds, N-(5-(tert-butyl) isoxazol-3-yl)-N'-(4-(7-methoxyimidazo[1,2-a]pyridin-2-yl)phenyl) urea (16i), displayed acceptable aqueous solubility, desirable pharmacokinetic profile and high cytotoxicity selectivity against MV4-11 cells. This compound can inhibit phosphorylation of FLT3 and induce apoptosis in a concentration-dependent manner. Further in vivo antitumor studies showed that 16i led to complete tumor regression in the MV4-11 xenograft model at a dose of 60 mg/kg/d while without observable body weight loss. This study had provided us a new chemotype of FLT3 inhibitors as novel therapic candidates for AML. (C) 2015 Published by Elsevier Ltd.
• DMSO–POCl3: a reagent for methylthiolation of imidazo[1,2-a]pyridines and other imidazo-fused heterocycles
  作者：Shashikant M. Patil、Sarang Kulkarni、Malcolm Mascarenhas、Rajiv Sharma、S. Mohana Roopan、Abhijit Roychowdhury

  DOI：10.1016/j.tet.2013.07.017

  日期：2013.9

  A practical and metal free method for methylthiolation of imidazo[1,2-a]pyridines and other imidazo-fused heterocycles using DMSO-POCl3 complex is reported. The reactions are carried out at room temperature that give the corresponding methylthiolated products in good to excellent yield. Further, its application to indole has been demonstrated. (C) 2013 Elsevier Ltd. All rights reserved.
• PHENYL-SUBSTITUTED IMIDAZOPYRIDINES
  申请人：Ortho McNeil Pharmaceuticals, Inc.

  公开号：EP1268478A2

  公开（公告）日：2003-01-02
• US6908929B2
  申请人：——

  公开号：US6908929B2

  公开（公告）日：2005-06-21