N'-[(E)-(4-nitrophenyl)methylidene]-2-pyrazinecarbohydrazide | 1206198-63-1

• 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: N'-[(E)-(4-nitrophenyl)methylidene]-2-pyrazinecarbohydrazide
• 英文别名: N'-[(1E)-(4-nitrophenyl)methylidene]pyrazine-2-carbohydrazide；LASSBio-1194；N'-[(E)-(4-nitrophenyl)methylidene]pyrazine-2-carbohydrazide；N-[(E)-(4-nitrophenyl)methylideneamino]pyrazine-2-carboxamide
• CAS: 1206198-63-1
• 化学式: C₁₂H₉N₅O₃
• 分子量: 271.235
• InChiKey: WYNIAZGJCLHKPV-VIZOYTHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N'-[(E)-(4-nitrophenyl)methylidene]-2-pyrazinecarbohydrazide 、 碘甲烷 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以58%的产率得到N-methyl-N'-(4-nitrobenzylidene)pyrazine-2-carbohydrazide
  参考文献：
  名称：

  FiveN′-benzylidene-N-methylpyrazine-2-carbohydrazides

  摘要：

  化合物N′-亚苄基-N-甲基吡嗪-2-甲酰肼，C13H12N4O，（IIa），N′-（2-甲氧基亚苄基）-N-甲基吡嗪-2-甲酰肼、C14H14N4O2，（IIb），N′-（4-氰基亚苄基）-N-甲基吡嗪-2-甲酰肼二水合物，C14H11N5O-2H2O，（IIc）、N-甲基-N′-（2-硝基亚苄基）吡嗪-2-甲酰肼，C13H11N5O3，(IId) 和 N-甲基-N′-（4-硝基亚苄基）吡嗪-2-甲酰肼，C13H11N5O3，(IIe) 吡嗪环和苯环之间的二面角在 55-78° 之间。这些甲基化吡嗪-2-甲酰肼具有由弱 C-H...O/N 氢键形成的超分子结构，只有水合的 (IIc) 除外。所有五种化合物都存在 π-π 堆叠相互作用。将其中三种结构与它们的非甲基化对应物进行比较，发现吡嗪环和苯环之间的二面角范围为 0-6°。

  DOI：

  10.1107/s0108270113010056
• 作为产物：
  描述：

  吡嗪-2-甲酰肼 、 对硝基苯甲醛 以 乙醇 、 水 为溶剂， 以67%的产率得到N'-[(E)-(4-nitrophenyl)methylidene]-2-pyrazinecarbohydrazide
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of N′-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide derivatives

  摘要：

  The present article describes a series of twenty-six N'-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide (4-29), which were synthesized and evaluated for their cell viabilities in non infected and infected macrophages with Mycobacterium bovis Bacillus Calmette-Guerin (BCG). Afterwards, the non-cytotoxic compounds (4, 6, 8, 15, 21, 23, 24, 27 and 28) were assessed against Mycobacterium tuberculosis ATCC 27294 using the micro plate Alamar Blue assay (MABA) and the activity expressed as the minimum inhibitory concentration (MIC) in mu g/mL. The compounds 6, 23, 27 and 28 exhibited a significant activity (50-100 mu g/mL) when compared with first line drugs such as pyrazinamide and were not cytotoxic in their respective MIC values. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.08.009

文献信息

• Synthesis and antimycobacterial activity of N′-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide derivatives
  作者：Fátima M.F. Vergara、Camilo H. da S. Lima、Maria das Graças M. de O. Henriques、André L.P. Candéa、Maria C.S. Lourenço、Marcelle de L. Ferreira、Carlos R. Kaiser、Marcus V.N. de Souza

  DOI：10.1016/j.ejmech.2009.08.009

  日期：2009.12

  The present article describes a series of twenty-six N'-[(E)-(monosubstituted-benzylidene)]-2-pyrazinecarbohydrazide (4-29), which were synthesized and evaluated for their cell viabilities in non infected and infected macrophages with Mycobacterium bovis Bacillus Calmette-Guerin (BCG). Afterwards, the non-cytotoxic compounds (4, 6, 8, 15, 21, 23, 24, 27 and 28) were assessed against Mycobacterium tuberculosis ATCC 27294 using the micro plate Alamar Blue assay (MABA) and the activity expressed as the minimum inhibitory concentration (MIC) in mu g/mL. The compounds 6, 23, 27 and 28 exhibited a significant activity (50-100 mu g/mL) when compared with first line drugs such as pyrazinamide and were not cytotoxic in their respective MIC values. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Synthesis and pharmacological evaluation of pyrazine N-acylhydrazone derivatives designed as novel analgesic and anti-inflammatory drug candidates
  作者：Yolanda Karla Cupertino da Silva、Cristina Villarinho Augusto、Maria Letícia de Castro Barbosa、Gabriela Muniz de Albuquerque Melo、Aline Cavalcanti de Queiroz、Thays de Lima Matos Freire Dias、Walfrido Bispo Júnior、Eliezer J. Barreiro、Lídia Moreira Lima、Magna Suzana Alexandre-Moreira

  DOI：10.1016/j.bmc.2010.06.002

  日期：2010.7

  In this paper, we report the synthesis and pharmacological evaluation of pyrazine N-acylhydrazone (NAH) derivatives (2a-s) designed as novel analgesic and anti-inflammatory drug candidates. This series was planned by molecular simplification of prototype 1 (LASSBio-1018), previously described as a nonselective cyclooxygenase inhibitor. Derivatives 2a-s were evaluated in several animal models of pain and inflammation, standing-out compound 2o (2-N'-[(E)-(3,4,5-trimethoxyphenyl) methylidene]-2-pyrazinecarbohydrazide; LASSBio-1181), that was also active in a murine model of chronic inflammation (i.e., adjuvant-induced arthritis test in rats) and can be considered a new analgesic and anti-inflammatory lead for drug development. Published by Elsevier Ltd.
• Five<i>N</i>′-benzylidene-<i>N</i>-methylpyrazine-2-carbohydrazides
  作者：Ligia R. Gomes、John Nicolson Low、Ana S. M. C. Rodrigues、James L. Wardell、Camillo H. da Silva Lima、Marcus V. N. de Souza

  DOI：10.1107/s0108270113010056

  日期：2013.5.15

  The compoundsN′-benzylidene-N-methylpyrazine-2-carbohydrazide, C₁₃H₁₂N₄O, (IIa),N′-(2-methoxybenzylidene)-N-methylpyrazine-2-carbohydrazide, C₁₄H₁₄N₄O₂, (IIb),N′-(4-cyanobenzylidene)-N-methylpyrazine-2-carbohydrazide dihydrate, C₁₄H₁₁N₅O·2H₂O, (IIc),N-methyl-N′-(2-nitrobenzylidene)pyrazine-2-carbohydrazide, C₁₃H₁₁N₅O₃, (IId), andN-methyl-N′-(4-nitrobenzylidene)pyrazine-2-carbohydrazide, C₁₃H₁₁N₅O₃, (IIe), have dihedral angles between the pyrazine rings and the benzene rings in the range 55–78°. These methylated pyrazine-2-carbohydrazides have supramolecular structures which are formed by weak C—H...O/N hydrogen bonds, with the exception of (IIc) which is hydrated. There are π–π stacking interactions in all five compounds. Three of these structures are compared with their nonmethylated counterparts, which have dihedral angles between the pyrazine rings and the benzene rings in the range 0–6°.

  化合物N′-亚苄基-N-甲基吡嗪-2-甲酰肼，C13H12N4O，（IIa），N′-（2-甲氧基亚苄基）-N-甲基吡嗪-2-甲酰肼、C14H14N4O2，（IIb），N′-（4-氰基亚苄基）-N-甲基吡嗪-2-甲酰肼二水合物，C14H11N5O-2H2O，（IIc）、N-甲基-N′-（2-硝基亚苄基）吡嗪-2-甲酰肼，C13H11N5O3，(IId) 和 N-甲基-N′-（4-硝基亚苄基）吡嗪-2-甲酰肼，C13H11N5O3，(IIe) 吡嗪环和苯环之间的二面角在 55-78° 之间。这些甲基化吡嗪-2-甲酰肼具有由弱 C-H...O/N 氢键形成的超分子结构，只有水合的 (IIc) 除外。所有五种化合物都存在 π-π 堆叠相互作用。将其中三种结构与它们的非甲基化对应物进行比较，发现吡嗪环和苯环之间的二面角范围为 0-6°。