2-(4-硝基苯基)-咪唑[1,2-a]并嘧啶 | 28266-96-8

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-硝基苯基)-咪唑[1,2-a]并嘧啶
• 中文别名: 2-(4-硝苯基)-咪唑并[1,2-A]嘧啶
• 英文名称: 2-(4-nitrophenyl)imidazo[1,2-a]pyrimidine
• 英文别名: 2-(p-Nitrophenyl)-imidazo<1,2-a>pyrimidin
• CAS: 28266-96-8
• 化学式: C₁₂H₈N₄O₂
• mdl: MFCD00602988
• 分子量: 240.221
• InChiKey: VUTPRDYSRJDBRS-UHFFFAOYSA-N

物化性质

• 熔点：
  >370 °C
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(4-硝基苯基)-咪唑[1,2-a]并嘧啶 在 镍 氢气 作用下， 以 乙醇 为溶剂， 生成 4-{咪唑并[1,2-A]嘧啶-2-基}苯胺
  参考文献：
  名称：

  2-芳基和2-芳氧基甲基咪唑并[1,2- a ]吡啶的制备及相关化合物

  摘要：

  一系列取代的2-芳基咪唑并[1,2-α]吡啶已被制备，其中多种取代基被引入在苯环的4'位和在3，5的，6或7位杂环。大多数实例在4'-位具有乙酰氨基，溴，氰基或甲酰基取代基。还已经制备了类似的咪唑并[ 2，1- b ]噻唑和咪唑并[1,2- a ]嘧啶。制备了由咪唑的4'-甲酰基苯氧基甲基衍生物，吡啶，噻唑，苯并咪唑和环取代的咪唑并[1,2- a ]吡啶的三个位置异构体组成的另一系列化合物。还制备了咪唑和咪唑并[1,2- a ]吡啶的2-（4'-甲酰基苯基乙烯基）衍生物。

  DOI：

  10.1002/jhet.5570250119
• 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)- 以50%的产率得到
  参考文献：
  名称：

  SALDABOL N. O.; LANDO O. E., XIMIYA GETEROTSIKL. SOEDIN. 1978, HO 2,

  摘要：

  DOI：

文献信息

• Synthesis and Antibacterial Activity of Some Imidazo(1,2-a)pyrimidine Derivatives.
  作者：Yveline RIVAL、Gerard GRASSY、Georges MICHEL

  DOI：10.1248/cpb.40.1170

  日期：——

  A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The "in vitro" antibacterial activity of these compounds and their corresponding alpha-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.

  合成了75种咪唑并[1,2-a]嘧啶衍生物。据报道，这些化合物及其相应的α-溴代酮对多种革兰氏（+），革兰氏（-）细菌和分枝杆菌属物种具有“体外”抗菌活性。一些制备的衍生物表现出有效的抗微生物活性。
• Sequential Regioselective Diorganochalcogenations of Imidazo[1,2-<i>a</i>]pyrimidines Using I₂/H₃PO₄ in Dimethylsulfoxide
  作者：Anne Roly Obah Kosso、Youssef Kabri、Julie Broggi、Sébastien Redon、Patrice Vanelle

  DOI：10.1021/acs.joc.9b02963

  日期：2020.3.6

  The dichalcogenation of imidazoheterocycles led to the first functionalization of imidazo[1,2-a]pyrimidine cores on the C6-position. The methodology, involving iodine/dimethylsulfoxide oxidation of diaryldichalcogenides, started with C3-chalcogenation, followed by C6 selanylation, activated in acidic medium. This novel sequential dichalcogenation strategy proceeded efficiently with excellent regioselectivity

  咪唑杂环的二卤代化作用导致咪唑[1,2-a]嘧啶核在C6-位上首次官能化。该方法涉及碘化二芳基二卤化碘的碘/二甲基亚砜，该方法首先在酸性介质中活化C3-硫属元素化，然后进行C6硒基化。这种新颖的顺序二硫代化策略以优异的区域选择性和产率有效进行。
• LIGANDS FOR AGGREGATED TAU MOLECULES
  申请人：Kemp Steven John

  公开号：US20110171739A1

  公开（公告）日：2011-07-14

  Provided are certain benzothiazole, imidazothiazole, imidazopyrimidine and imidazopyridine compounds, including, for example: formula (I) and pharmaceutically and physiologically acceptable salts, hydrates, and solvates thereof. Such compounds can be used as diagnostic ligands or labels of tau protein and PHF.

  提供了某些苯并噻唑、咪唑噻唑、咪唑嘧啶和咪唑吡啶化合物，包括例如：式（I）和其药学和生理学上可接受的盐、水合物和溶剂化物。这些化合物可用作tau蛋白和PHF的诊断配体或标记。
• Beneficial effects of a new neuroprotective compound in neuronal cells and MPTP-administered mouse model of Parkinson's disease
  作者：Izumi Kato、Yudai Ogawa、Fumika Yakushiji、Jiro Ogura、Masaki Kobayashi、Naoya Shindo、Satoshi Ichikawa、Katsumi Maenaka、Masahiro Sakaitani

  DOI：10.1039/d3cc03069e

  日期：——

  A new compound, a derivative of 3,4,5-trimethoxy-N-phenyl benzamide bearing an 8′′-methylimidazopyridine moiety, is found to demonstrate neuroprotective effects by preventing cell death caused by oxidative stress.

  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。
• Structure−Activity Relationship of 4(5)-Aryl-2-amino-1<i>H</i>-imidazoles, <i>N</i>1-Substituted 2-Aminoimidazoles and Imidazo[1,2-<i>a</i>]pyrimidinium Salts as Inhibitors of Biofilm Formation by <i>Salmonella</i> Typhimurium and <i>Pseudomonas aeruginosa</i>
  作者：Hans P. L. Steenackers、Denis S. Ermolat’ev、Bharat Savaliya、Ami De Weerdt、David De Coster、Anamik Shah、Erik V. Van der Eycken、Dirk E. De Vos、Jozef Vanderleyden、Sigrid C. J. De Keersmaecker

  DOI：10.1021/jm1011148

  日期：2011.1.27

  A library of 112 4(5)-aryl-2-amino-1H-imidazoles, 4,5-diphenyl-2-amino-1H-imidazoles, and N1-substituted 4(5)-phenyl-2-aminoimidazoles was synthesized and tested for the antagonistic effect against biofilm formation by Salmonella Typhimurium and Pseudomonas aeruginosa. The substitution pattern of the 4(5)phenyl group and the nature of the N1-substituent were found to have a major effect on the biofilm inhibitory activity. The most active compounds of this series were shown to inhibit the biofilm formation at low micromolar concentrations. Furthermore, the influence of 6 imidazo[1,2-a]pyrimidines and 18 imidazo[1,2-a]pyrimidinium salts on the biofilm formation was tested. These compounds are the chemical precursors of the 2-aminoimidazoles in our synthesis pathway. A good correlation was found between the activity of the imidazo[1,2-a]pyrimidinium salts and their corresponding 2-aminoimidazoles, supporting the hypothesis that the imidazo[1,2-a]pyrimidinium salts are possibly cleaved by cellular nucleophiles to form the active 2-aminoimidazoles. However, the imidazo[1,2-a]pyrimidines did not show any biofilm inhibitory activity, indicating that these molecules are not susceptible to in situ degradation to 2-aminoimidazoles. Finally, we demonstrated the lack of biofilm inhibitory activity of an array of 37 2N-substituted 2-aminopyrimidines, which are the chemical precursors of the imidazo[1,2-a]pyrimidinium salts in our synthesis pathway.