N-(4-fluorophenyl)pyrazine-2-carboxamide | 320582-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-fluorophenyl)pyrazine-2-carboxamide
• CAS: 320582-39-6
• 化学式: C₁₁H₈FN₃O
• mdl: MFCD00981048
• 分子量: 217.202
• InChiKey: GYYWBZYUXVRWBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲酸吡嗪 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(4-fluorophenyl)pyrazine-2-carboxamide
  参考文献：
  名称：

  N-芳基吡嗪和N，N'-烷基-二基吡嗪-2-羧酰胺衍生物的合成及抗结核评价

  摘要：

  合成了两个系列的吡嗪酰胺（PZA）衍生物，并评估了它们对结核分枝杆菌H37Rv的体外抗菌活性。一些化合物表现出的最小抑菌浓度活性为50–100μg/ mL，高于Alamar Blue分析中的一线抗结核药物PZA（> 100μg/ mL）。所获得的活性可以被认为是有希望的结果，其将这些化合物表征为开发新的抗结核药的良好起点。

  DOI：

  10.1002/jhet.921

文献信息

• Effect of halogen bonding interaction on supramolecular assembly of halogen-substituted phenylpyrazinamides
  作者：Hamid Reza Khavasi、Alireza Azhdari Tehrani

  DOI：10.1039/c3ce40093j

  日期：——

  A series of halogen-substituted phenylpyrazinamides have been synthesized and crystallographically characterized in order to investigate the effect of halogen bonding interaction on supramolecular assembly of N-phenylpyrazine-2-carboxamide derivatives. The notable feature in crystal structures of meta- and para-iodinated, brominated and chlorinated compounds is that there is a tendency to form a halogen bonding synthon between adjacent halophenyl and prazine/halophenyl rings. Influence of these halogen bonding interactions on supramolecular assemblies have been discussed with the help of geometrical analysis and theoretical calculations. The X⋯N halogen bonding distances are 2.2–7.7% shorter than the sum of the van der Waals radii of the nitrogen and halogen atoms. Also, theoretical methods show the N⋯X halogen bonding energies within a range of −9.43 to −23.67 kJ mol−1. Our studies show that the selection of halogen atom as well as the position of substitution on phenylpyrazinamide compound may be important for crystal design based on halogen bonding.

  合成了一系列卤素取代的苯基吡嗪氨基酸酰胺，并进行了晶体学表征，以研究卤素键相互作用对N-苯基吡嗪-2-羧酰胺衍生物超分子组装的影响。meta-和para-碘化、溴化及氯化化合物的晶体结构中的一个显著特征是，邻近的卤素苯基和吡嗪/卤素苯基环之间有形成卤素键合成体的趋势。利用几何分析和理论计算，讨论了这些卤素键相互作用对超分子组装的影响。X⋯N卤素键距比氮和卤素原子的范德华半径之和短2.2%–7.7%。此外，理论方法显示N⋯X卤素键能量在−9.43到−23.67 kJ mol−1之间。我们的研究表明，卤素原子的选择以及在苯基吡嗪氨基酸酰胺化合物上的取代位置可能对基于卤素键的晶体设计至关重要。
• Strengthening N⋯X halogen bonding via nitrogen substitution in the aromatic framework of halogen-substituted arylpyrazinamides
  作者：Hamid Reza Khavasi、Mahdieh Hosseini、Alireza Azhdari Tehrani、Soheila Naderi

  DOI：10.1039/c3ce41856a

  日期：——

  The importance of N⋯X halogen bonding in a series of N-(5-halo-2-pyridinyl)pyrazine-2-carboxamides has been investigated by different methods.

  一系列N-(5-卤代-2-吡啶基)吡嗪-2-羧酰胺化合物中N⋯X卤素键的重要性已通过不同方法进行了研究。
• An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
  作者：Tarek S. Ibrahim、Israa A. Seliem、Siva S. Panda、Amany M. M. Al-Mahmoudy、Zakaria K. M. Abdel-Samii、Nabil A. Alhakamy、Hani Z. Asfour、Mohamed Elagawany

  DOI：10.3390/molecules25112501

  日期：——

  straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction

  使用通用的苯并三唑化学完成了在水中直接、温和且经济高效地合成各种芳基酰胺。在室温下以及在微波辐射下，在水中实现了各种胺的酰化。开发的协议展开了氨基酸芳基酰胺、药物偶联物和苯并咪唑的合成。环保合成、反应时间短、后处理简单、收率高、条件温和、无外消旋化是该协议的主要优点。
• Preparation of Pyrazine Carboxamides: A Reaction Involving <i>N</i>-Heterocyclic Carbene (NHC) Intermediates
  作者：Rajasekhar Reddy Naredla、Barada P. Dash、Douglas A. Klumpp

  DOI：10.1021/ol402200x

  日期：2013.9.20

  In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product

  在2，3-吡嗪二羧酸酐与胺和苯胺的反应中，形成吡嗪羧酰胺的产率高至优异。提出了涉及酸酐的开环和杂环的脱羧的机理。基于其他类似的杂环脱羧，这表明涉及N-杂环卡宾中间体导致产物。
• Synthesis and antimycobacterial evaluation of substituted pyrazinecarboxamides
  作者：Martin Dolezal、Pavlina Cmedlova、Lukas Palek、Jarmila Vinsova、Jiri Kunes、Vladimir Buchta、Josef Jampilek、Katarina Kralova

  DOI：10.1016/j.ejmech.2007.07.013

  日期：2008.5

  Unsubstituted, halogenated and/or alkylated pyrazine-2-carboxylic acid amides connected via -CONH- bridge with substituted anilines were synthesized using currently known synthetic pathways. The synthetic approach, analytical, spectroscopic, lipophilicity and biological data of 20 newly synthesized compounds are presented. Structure-activity relationships among the chemical structures, the antimycobacterial, antifungal, photosynthesis inhibiting and antialgal activity of the evaluated substituted N-phenylpyrazine-2-carboxamides are discussed. 5-tert-Butyl-6-chloro-N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (19) has shown the highest activity against Mycobacterium tuberculosis H(37)Rv (MIC = 3.13 mu g/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (14, MIC = 62.5 mu mol/mL). The highest reduction of chlorophyll content in Chlorella vulgaris was found for pyrazine-2-carboxylic acid (3-trifluoromethylphenyl)amide (9, IC50 = 12.1 mu mol/L). (C) 2007 Elsevier Masson SAS. All rights reserved.