3-chloro-5-cyano-2-pyrazinecarboxamide | 132274-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-chloro-5-cyano-2-pyrazinecarboxamide
• 英文别名: 3-chloro-5-cyanopyrazine-2-carboxamide
• CAS: 132274-79-4
• 化学式: C₆H₃ClN₄O
• 分子量: 182.569
• InChiKey: RCYANRPRMFVJGL-UHFFFAOYSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  343.1±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-5-cyano-2-pyrazinecarboxamide 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3-(methylamino)pyrazine-2,5-dicarbonitrile
  参考文献：
  名称：

  N-取代的3-氨基吡嗪-2,5-二甲腈的合成及抗分枝杆菌作用

  摘要：

  合成了一系列与吡嗪酰胺有关的14种新化合物，并通过分析数据进行了表征，并筛选了针对结核分枝杆菌，堪萨斯分枝杆菌和两种鸟分枝杆菌的体外抗分枝杆菌活性。该系列由通过各种非芳族胺（烷基胺，环烷基胺和杂环胺）对氯的亲核取代而衍生自3-氯吡嗪-2,5-二腈的N-取代的3-氨基吡嗪-2,5-二腈。在烷基氨基衍生物中发现了值得注意的针对结核分枝杆菌的抗分枝杆菌活性，例如3-（庚基氨基）吡嗪-2,5-二甲腈抑制的结核分枝杆菌。在MIC = 51μmol/ L时。3-（己基氨基）吡嗪-2,5-二碳腈在MIC = 218μmol / L时抑制堪萨斯分枝杆菌。讨论了基本的结构-活动关系。包括该系列中计算出的和实验确定的亲脂性参数之间的比较。

  DOI：

  10.1016/j.bmcl.2011.12.129
• 作为产物：
  描述：

  吡嗪酰胺 在 ammonium peroxydisulfate 、 双氧水 、 溶剂黄146 作用下， 生成 3-chloro-5-cyano-2-pyrazinecarboxamide
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution

  摘要：

  A series of 19 new compounds related to pyrazinamide were synthesized, characterized with analytical data and screened for in vitro whole cell antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium kansasii and two types of Mycobacterium avium. The series consisted of 3( benzylamino)-5-cyanopyrazine-2-carboxamides and 3-(benzylamino)pyrazine-2,5-dicarbonitriles with various substituents on the phenyl ring. RP-HPLC method was used to determine the lipophilicity of the prepared compounds. Nine compounds exerted similar or better activity against Mycobacterium tuberculosis compared to pyrazinamide (MIC = 6.25-12.5 mu g/mL). 3-(Benzylamino)pyrazine-2,5-dicarbonitrile inhibited all of the tested mycobacterial strains with MIC within the range 12.5-25 mu g/mL. Although not the most active, 4-NH2 substituted compounds possessed the lowest in vitro cytotoxicity (hepatotoxicity), leading to selectivity index SI = 5.5 and SI > 21. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.052

文献信息

• Synthesis, Antimycobacterial and Antifungal Evaluation of 3-Arylaminopyrazine-2,5-dicarbonitriles
  作者：Lukáš Palek、Jaroslav Dvořák、Michaela Svobodová、Vladimír Buchta、Josef Jampílek、Martin Doležal

  DOI：10.1002/ardp.200700119

  日期：2008.1

  This paper describes preparation and biological evaluation of pyrazinamide analogues. Pyrazinamide with its simple structure gives a good opportunity for further modification regarding an increase of its antimycobacterial activity. We prepared a series of compounds derived from pyrazine‐2,5‐dicarbonitrile with arylamino substitution in position 3. All compounds were assayed in vitro against major Mycobacterium

  本文介绍了吡嗪酰胺类似物的制备和生物学评价。吡嗪酰胺结构简单，为进一步修饰提高其抗分枝杆菌活性提供了良好的机会。我们制备了一系列衍生自吡嗪 - 2,5 - 二腈且在 3 位具有芳基氨基取代的化合物。所有化合物均在体外针对主要分枝杆菌和各种真菌物种进行了测定。在 3 - [3- (三氟甲基) 苯基] 氨基} 吡嗪 - 2,5 - 二甲腈 11 中发现的活性最好，对结核分枝杆菌 H37Rv 的值为 6.25 μmol - 1，对次要的分枝杆菌病原体具有中等活性。
• Exploring the detailed spectroscopic characteristics, chemical and biological activity of two cyanopyrazine-2-carboxamide derivatives using experimental and theoretical tools
  作者：Shargina Beegum、Y. Sheena Mary、Y. Shyma Mary、Renjith Thomas、Stevan Armaković、Sanja J. Armaković、Jan Zitko、Martin Dolezal、C. Van Alsenoy

  DOI：10.1016/j.saa.2019.117414

  日期：2020.1

  transformed infrared (FT-IR) and Raman spectra, nuclear magnetic resonance (NMR) spectra, and ultraviolet (UV) absorptions and have compared them with the simulated computational spectra and found that they are in the agreeable range. Simulated hyperpolarisability values are used to obtain the nonlinear optic (NLO) activity of the compound, to be used in organic electronic materials. The charge transfer and

  本文介绍了两种新的吡嗪化合物的光谱和计算研究。为了确定化合物的结构和功能性质，我们使用了傅立叶变换红外（FT-IR）和拉曼光谱，核磁共振（NMR）光谱和紫外（UV）吸收量，并将它们与模拟计算值进行了比较。光谱，发现它们在可接受的范围内。模拟的超极化率值用于获得该化合物的非线性光学（NLO）活性，并将其用于有机电子材料中。通过使用时变密度泛函理论（TD-DFT）对电子光谱进行仿真，研究了电荷转移和相关特性。自然跃迁轨道（NTO）提供有关分子的哪个区域更多地参与电子跃迁的信息，并且已基于电子密度变化分析了最低能量激发的电荷转移性质。分子动力学模拟提供了有关溶液中分子行为的信息。前沿轨道分析和对各种反应性描述符（如ALIE和Fukui）的研究为反应性方面提供了深厚的知识。还进行了分子对接研究标题分子之间的相互作用并表现出对 分子动力学模拟提供了有关溶液中分子行为的信息。前沿轨道分析和对各种反应性
• Synthesis and Antituberculotic Activity of Some Substituted 3-Arylamino-5-cyano-2-pyrazinecarboxamides
  作者：Martin Doležal、Jiří Hartl、Antonín Lyčka、Vladimír Buchta、Želmíra Odlerová

  DOI：10.1135/cccc19951236

  日期：——

  Nucleophilic substitution of 3-chloro-5-cyano-2-pyrazinecarboxamide by substituted anilines afforded substituted 3-arylamino-5-cyano-2-pyrazinecarboxamides I-X. The structures of compounds were confirmed by elemental analysis, UV, IR and ¹H NMR spectra. The assessment of in vitro antimycotic and antimycobacterial activities of the compounds was carried out. The highest antituberculotic activity against M. tuberculosis in this series was shown by 3-anilino- 5-cyano-2-pyrazinecarboxamide (I), whose efficacy was the same as that of pyrazinecarboxamide.

  对3-氯-5-氰基-2-吡嗪羧酰胺进行亲核取代反应，使用取代的苯胺得到了取代的3-芳基氨基-5-氰基-2-吡嗪羧酰胺I-X。通过元素分析、紫外线、红外线和1H核磁共振光谱证实了化合物的结构。对化合物进行了体外抗真菌和抗结核活性评估。在这个系列中，3-苯胺基-5-氰基-2-吡嗪羧酰胺（I）表现出对结核分枝杆菌的最高抗菌活性，其功效与吡嗪羧酰胺相同。
• Synthesis and Antituberculotic Properties of Some Substituted Pyrazinecarbothioamides
  作者：Martin Doležal、Jiří Hartl、Antonín Lyčka、Vladimír Buchta、Želmíra Odlerová

  DOI：10.1135/cccc19961102

  日期：——

  A series of N-substituted 3-amino-5-thiocarbamoyl-2-pyrazinecarboxamides was prepared. The structure of compounds was confirmed by elemental analysis, IR and ¹H NMR spectra. The results of in vitro antifugal and antimycobacterial susceptibility testing shown no activity against pathogenic fungi and some effect on mycobacteria. The highest antituberculotic activity (MIC within 25-50 mg ml^-1) against Mycobacterium tuberculosis and other mycobacterial strains in this series was shown by 3-(3-hydroxyphenylamino)-5-thiocarbamoyl-2-pyrazinecarboxamide. The antituberculotic activity of these compounds is mostly influenced by the presence of the thioamide moiety.

  制备了一系列N取代的3-氨基-5-硫代氨基甲酰基-2-吡嗪羧酰胺。通过元素分析，红外光谱和1H NMR光谱确认了化合物的结构。体外抗真菌和抗结核杆菌敏感性试验结果表明，这些化合物对病原真菌没有活性，对结核分枝杆菌有一定的作用。在这个系列中，对结核分枝杆菌和其他分枝杆菌菌株的最高抗结核活性（最小抑菌浓度在25-50 mg ml-1之间）是由3-(3-羟基苯氨基)-5-硫代氨基甲酰基-2-吡嗪羧酰胺表现出来的。这些化合物的抗结核活性主要受硫代酰胺基团的影响。
• Preparation of Some N-Substituted 3-Amino-5-cyano-2-pyrazinecarboxamides
  作者：Martin Doležal、Jiří Hartl、Miloš Macháček

  DOI：10.1135/cccc19942562

  日期：——

  During the course of a search for new antimycotic agents a series of 3-amino-5-cyano-2-pyrazinecarboxamides I - XI have been synthesized. The prepared compounds were tested for their antimycotic activity. The MIC of these in the form of dimethyl sulfoxide solutions was measured against Candida albicans ATCC 44859, Candida tropicalis 156, Candida krusei E28, Candida glabrata 20/I, Trichosporon beigelii 1188, Trichophyton mentagrophytes 445, Aspergillus fumigatus 231, and Absidia corymbifera 272. None of the compounds studied was particularly effective.

  在寻找新型抗真菌药物的过程中，合成了一系列3-氨基-5-氰基-2-吡嗪羧酰胺-。测试了这些合成化合物的抗真菌活性。使用二甲基亚砜溶液形式测定了这些化合物对Candida albicans ATCC 44859、Candida tropicalis 156、Candida krusei E28、Candida glabrata 20/I、Trichosporon beigelii 1188、Trichophyton mentagrophytes 445、Aspergillus fumigatus 231和Absidia corymbifera 272的最小抑菌浓度（MIC）。研究的化合物都没有表现出特别的有效性。