5-cyano-3-((4-methylbenzyl)amino)pyrazine-2-carboxamide | 1418269-51-8

• 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: 5-cyano-3-((4-methylbenzyl)amino)pyrazine-2-carboxamide
• 英文别名: CMBAPC；5-Cyano-3-(p-tolylmethylamino)pyrazine-2-carboxamide；5-cyano-3-[(4-methylphenyl)methylamino]pyrazine-2-carboxamide
• CAS: 1418269-51-8
• 化学式: C₁₄H₁₃N₅O
• 分子量: 267.29
• InChiKey: BWCYPUJZYMFNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吡嗪酰胺 在 ammonium peroxydisulfate 、 双氧水 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 5-cyano-3-((4-methylbenzyl)amino)pyrazine-2-carboxamide
  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

• 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