N'-(1-(1H-benzo[d]imidazol-2-yl)ethylidene)-2-cyanoacetohydrazide | 1338245-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N'-(1-(1H-benzo[d]imidazol-2-yl)ethylidene)-2-cyanoacetohydrazide
• 英文别名: N-[1-(1H-benzimidazol-2-yl)ethylideneamino]-2-cyanoacetamide
• CAS: 1338245-65-0
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: XAVKDFKONPFVHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(1-(1H-benzo[d]imidazol-2-yl)ethylidene)-2-cyanoacetohydrazide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((3-fluorobenzylidene)amino)-4-(3-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  轻松合成带有2-吡啶酮衍生物的苯并咪唑作为潜在的抗菌剂

  摘要：

  摘要合成了一系列带有2-吡啶酮5a-k的苯并咪唑，并使用常规肉汤稀释法体外评估了它们作为抗菌剂的活性。抗菌研究的结果表明，与标准药物氯霉素和酮康唑相比，化合物5b，5c，5j和5k表现出显着的抗菌活性，而化合物5d则作为更有效的抗真菌剂出现。观察到，感应吸电子基团的存在显着增强了新合成化合物的抗菌活性。细胞毒性研究表明，所有测试化合物均未显示任何明显的细胞毒性作用。

  DOI：

  10.1016/j.cclet.2013.11.026
• 作为产物：
  描述：

  氰乙酰肼 、 2-乙酰苯并咪唑 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以70%的产率得到N'-(1-(1H-benzo[d]imidazol-2-yl)ethylidene)-2-cyanoacetohydrazide
  参考文献：
  名称：

  轻松合成带有2-吡啶酮衍生物的苯并咪唑作为潜在的抗菌剂

  摘要：

  摘要合成了一系列带有2-吡啶酮5a-k的苯并咪唑，并使用常规肉汤稀释法体外评估了它们作为抗菌剂的活性。抗菌研究的结果表明，与标准药物氯霉素和酮康唑相比，化合物5b，5c，5j和5k表现出显着的抗菌活性，而化合物5d则作为更有效的抗真菌剂出现。观察到，感应吸电子基团的存在显着增强了新合成化合物的抗菌活性。细胞毒性研究表明，所有测试化合物均未显示任何明显的细胞毒性作用。

  DOI：

  10.1016/j.cclet.2013.11.026

文献信息

• A search of novel antimicrobial based on benzimidazole and 2-pyridone heterocycles
  作者：N. C. Desai、Amit M. Dodiya、Niraj R. Shihory

  DOI：10.1007/s00044-011-9782-2

  日期：2012.9

  The increasing incidence of bacterial drug resistance imposes a new search on existing antimicrobial drugs leading to the development of new bioactive molecules. In continuation to this, the present article deals with the synthesis and antimicrobial activity of 1-(1-(1H-benzo[d]imidazol-2-yl)ethylideneamino)-6-(arylideneamino)-4-(2-hydroxyphenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitriles (4a-k). All newly synthesized compounds have been evaluated against two gram positive bacteria (Staphylococcus aureus, Streptococcus pyogenes), two gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa), and three fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using serial broth dilution method. Compounds reported in the present article bearing chloro and hydroxy groups exhibit very good to excellent antimicrobial activity. All the newly synthesized compounds have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectra.
• Synthesis, antibacterial and antitubercular activities of benzimidazole bearing substituted 2-pyridone motifs
  作者：N.C. Desai、N.R. Shihory、G.M. Kotadiya、Priyanka Desai

  DOI：10.1016/j.ejmech.2014.06.004

  日期：2014.7

  A series of benzimidazole bearing 2-pyridones 5a-r were synthesized and evaluated for their in vitro antibacterial and antitubercular activity. Further, all compounds were examined for their cytotoxic study on VERO cell line and characterized by well-known spectral techniques. It was observed that the compounds 5h, 5i, 5k, 5q and 5r were found to possess significant broad spectrum antibacterial activity (12.5-100 mu g/mL of MIC), while compounds 5g-5i, 5k and 5l proved to be the most potent antitubercular activity in range of 2.76-20.4 mu M of MIC at low level of cytotoxicity, indicating good selectivity. From SAR studies, lipophilic profile of compounds was remarkably vital for antibacterial activity, while MIC values of antitubercular activity could not be directly correlated with lipophilicity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Studies on Antimicrobial Evaluation of Some 1-((1-(1<i>H</i>-Benzo[<i>d</i>]imidazol-2-yl)ethylidene)amino)-6-((arylidene)amino)-2-oxo-4-phenyl-1, 2-dihydropyridine-3,5-dicarbonitriles
  作者：N. C. Desai、Niraj Shihory、Malay Bhatt、Bonny Patel、Tushar Karkar

  DOI：10.1080/00397911.2015.1102286

  日期：2015.12.2

  A new series of 1-((1-(1H-benzo[d]imidazol-2-yl)ethylidene)amino)-6-((arylidene)amino)-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles (4a-o) have been synthesized for the development of antimicrobial agents. Newly synthesized compounds were evaluated for their in vitro antibacterial activity against Gram-positive bacteria (Pseudomonas aeruginosa, Streptococcus pyogenes), Gram-negative bacteria (Escherichia coli, Staphylococcus aureus), and antifungal activity (Candida albicans, Aspergillus niger, Aspergillus clavatus). These compounds were characterized by infrared, H-1 NMR, C-13 NMR, and mass spectra. The synthesized compounds 4b, 4e, 4h, and 4k showed potent antimicrobial activity against tested microorganisms.