6-chloro-5-cyanopyrazine-2-carboxamide | 1280212-13-6

• 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: 6-chloro-5-cyanopyrazine-2-carboxamide
• CAS: 1280212-13-6
• 化学式: C₆H₃ClN₄O
• 分子量: 182.569
• InChiKey: PRXRCLLTOALRNI-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  375.3±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：

  6-chloro-5-cyanopyrazine-2-carboxamide 在 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 3-(4-aminobenzylamino)pyrazine-2,5-dicarbonitrile
  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
• 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 6-chloro-5-cyanopyrazine-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

• Synthesis and antimycobacterial properties of N-substituted 6-amino-5-cyanopyrazine-2-carboxamides
  作者：Jan Zitko、Martin Dolezal、Michaela Svobodova、Marcela Vejsova、Jiri Kunes、Radim Kucera、Petr Jilek

  DOI：10.1016/j.bmc.2010.12.054

  日期：2011.2

  A series of fifteen new compounds related to pyrazinamide (PZA) were synthesized, characterized with analytical data and screened for antimycobacterial, antifungal and antibacterial activity. The series consists of 6-chloro-5-cyanopyrazine-2-carboxamide and N-substituted 6-amino-5-cyanopyrazine-2-carboxamides, derived from the previous by nucleophilic substitution with various non-aromatic amines (alkylamines, cycloalkylamines, heterocyclic amines). Some of the compounds exerted antimycobacterial activity against Mycobacterium tuberculosis equal to pyrazinamide (12.5-25 mu g/mL). More importantly, 6-chloro-5-cyanopyrazine-2-carboxamide and 5-cyano-6-(heptylamino)pyrazine-2-carboxamide were active against Mycobacterium kansasii and Mycobacterium avium, which are unsusceptible to PZA. Basic structure-activity relationships are presented. Only weak antifungal and no antibacterial activity was detected. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and antimycobacterial evaluation of pyrazinamide derivatives with benzylamino substitution
  作者：Jan Zitko、Pavla Paterová、Vladimír Kubíček、Jana Mandíková、František Trejtnar、Jiří Kuneš、Martin Doležal

  DOI：10.1016/j.bmcl.2012.11.052

  日期：2013.1

  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.