2-(3-nitrophenyl)-1H-imidazo[1,2-a]pyrimidin-4-ium bromide | 1574306-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-nitrophenyl)-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
• CAS: 1574306-14-1
• 化学式: Br*C₁₂H₉N₄O₂
• 分子量: 321.133
• InChiKey: KLVNWIPBRXRXIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.92
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 在 palladium 10% on activated carbon 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.5h， 生成 N-(5-(3-aminophenyl)-1H-imidazol-2-yl)-3-chlorobenzamide
  参考文献：
  名称：

  THERAPEUTIC TARGETING OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 (IRAK4) IN CANCERS CHARACTERIZED BY REARRANGEMENTS IN THE MIXED LINEAGE LEUKEMIA GENE (MLL-r)

  摘要：

  揭示了治疗与混合系谱白血病基因（MLL-r）重排相关的癌症的方法，包括MLL-r白血病。这些方法通常包括给予治疗量的一个或多个治疗剂，其抑制白介素-1信号通路的一个或多个成员的生物活性，例如白介素-1受体相关激酶4（IRAK4）的抑制剂。

  公开号：

  US20170305901A1
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 2-溴-3'-硝基苯乙酮 以 乙腈 为溶剂， 反应 0.42h， 生成 2-(3-nitrophenyl)-1H-imidazo[1,2-a]pyrimidin-4-ium bromide
  参考文献：
  名称：

  THERAPEUTIC TARGETING OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 (IRAK4) IN CANCERS CHARACTERIZED BY REARRANGEMENTS IN THE MIXED LINEAGE LEUKEMIA GENE (MLL-r)

  摘要：

  揭示了治疗与混合系谱白血病基因（MLL-r）重排相关的癌症的方法，包括MLL-r白血病。这些方法通常包括给予治疗量的一个或多个治疗剂，其抑制白介素-1信号通路的一个或多个成员的生物活性，例如白介素-1受体相关激酶4（IRAK4）的抑制剂。

  公开号：

  US20170305901A1

文献信息

• Hypervalent Iodine Mediated Efficient Solvent-Free Regioselective Halogenation and Thiocyanation of Fused N-Heterocycles
  作者：Divakar Reddy Indukuri、Gal Reddy Potuganti、Manjula Alla

  DOI：10.1055/s-0037-1611856

  日期：2019.8

  2-a]pyridine/pyrimidine heterocycles has been achieved under solvent-free reaction conditions. Halogenations and thiocyanation of the heterocycles could be accomplished by simple grinding of reactants and hypervalent iodine reagents with the corresponding alkali metal or ammonium salts. The method has been extrapolated to a cleaner synthesis of brominated imidazo[1,2-a]pyridine/pyrimidine derivatives

  在无溶剂反应条件下实现了咪唑并[1,2-a]吡啶/嘧啶杂环的简便、快速、无金属的区域选择性卤化和硫氰化。杂环的卤化和硫氰化可以通过将反应物和高价碘试剂与相应的碱金属或铵盐简单研磨来完成。该方法已被外推到溴化咪唑并 [1,2-a] 吡啶/嘧啶衍生物的更清洁合成，从相应的杂环胺和取代的 α-溴酮开始，利用原位生成的 HBr 作为溴源。
• Substituted 4-phenyl-2-aminoimidazoles and 4-phenyl-4,5-dihydro-2-aminoimidazoles as voltage-gated sodium channel modulators
  作者：Nace Zidar、Žiga Jakopin、David J. Madge、Fiona Chan、Jan Tytgat、Steve Peigneur、Marija Sollner Dolenc、Tihomir Tomašić、Janez Ilaš、Lucija Peterlin Mašič、Danijel Kikelj

  DOI：10.1016/j.ejmech.2013.12.034

  日期：2014.3

  Voltage-gated sodium channels play an integral part in neurotransmission and their dysfunction is frequently a cause of various neurological disorders. On the basis of the structure of marine alkaloid clathrodin, twenty eight new analogs were designed, synthesized and tested for their ability to block human Na(v)1.3, Na(v)1.4 and Na(v)1.7 channels, as well as for their selectivity against human cardiac isoform Na(v)1.5, using automated patch clamp electrophysiological assay. Several compounds exhibited promising activities on different Na-v channel isoforms in the medium micromolar range and some of the compounds showed also moderate isoform selectivities. The most promising results were obtained for the Na(v)1.3 channel, for which four compounds were found to possess IC50 values lower than 15 mu M. All of the active compounds bind to the open-inactivated states of the channels and therefore act as state-dependent modulators. The obtained results validate the approach of using natural products driven chemistry for drug discovery starting points and represent a good foundation for future design of selective Na-v modulators. (C) 2013 Elsevier Masson SAS. All rights reserved.