2-hydroxybenzoic acid N'-(1H-pyrrol-2-ylmethylene)hydrazide | 19015-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxybenzoic acid N'-(1H-pyrrol-2-ylmethylene)hydrazide
• 英文别名: pyrrole-2-carboxaldehyde salicylhydrazone；PCSH；Pyrrol-2-carboxaldehyd-(2-hydroxy-benzoyl-hydrazon)；2-hydroxy-N-(1H-pyrrol-2-ylmethylideneamino)benzamide
• CAS: 19015-16-8
• 化学式: C₁₂H₁₁N₃O₂
• mdl: MFCD00560551
• 分子量: 229.238
• InChiKey: SSFAKFBVXKBZAY-UHFFFAOYSA-N

物化性质

• 熔点：
  222-223 °C (decomp)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 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：
  77.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxybenzoic acid N'-(1H-pyrrol-2-ylmethylene)hydrazide 、 copper dichloride 以 乙醇 为溶剂， 以57%的产率得到
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF ANTIBACTERIAL Co(II), Cu(II), Ni(II), AND Zn(II) COMPLEXES OF ACYLHYDRAZINE DERIVED PYRROLYL COMPOUNDS

  摘要：

  Acythydrazine derived pyrrolyl ligands and their metal [Co(II), Cu(II), Ni(II), and Zn(II)] complexes have been prepared and characterized on the basis of elemental analyses, magnetic moments, molar conductances and spectroscopic (electronic, IR, H-1 and C-13 NMR) data. All of these compounds function as tridentate ligands, with their deprotonated enolic form being preferred in the coordination to the metal ions. The title synthesized ligands and their metal(II) complexes have been screened for bactericidal activity against the pathogenic bacterial species Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, and it is shown that the metal complexes act as more active antibacterial agents than the uncomplexed ligands from which they derive.

  DOI：

  10.1081/sim-120003793
• 作为产物：
  描述：

  2-吡咯甲醛 、 水杨酰肼 以 水 为溶剂， 反应 2.0h， 以88.46%的产率得到2-hydroxybenzoic acid N'-(1H-pyrrol-2-ylmethylene)hydrazide
  参考文献：
  名称：

  吡咯-2-甲醛水杨腙 (PCSH) 的环保合成、光谱和计算研究及其应用

  摘要：

  摘要 在本文中，我们介绍了吡咯-2-甲醛水杨腙（PCSH）的环保合成及其分子结构解析、光谱分析和反应性评价。Pyrrole-2-carboxaldehyde 和水杨酰肼在水中进行缩合反应，以良好的收率 (88%) 生成 PCSH。量子化学计算的所有结果都很好地证实了实验结果。PCSH 已通过元素分析、FT-IR、1 H NMR、UV-可见光和 ESI-质谱法进行表征。通过使用标准基组 6–31 + g (d, p) 和附加基组 6D 和 10F 执行 B3LYP 泛函，对 PCSH 进行了密度泛函理论 (DFT) 计算。已在二面角 N1C5C6N7 周围观察到 PCSH 的两个最稳定的构象异构体。在 FT-IR 光谱中的 O-H 伸缩振动中观察到的红移表明存在分子内氢键。发现 syn-syn（闭合）syn-syn（开放）之间的旋转势垒为 2966.9 kcal/mol。在实验 1 H NMR

  DOI：

  10.1016/j.molstruc.2015.07.005

文献信息

• Synthesis and Investigation of Antimicrobial Activity of Some Nifuroxazide Analogues
  作者：Huda S. Alsaeedi、Nabila A. Aljaber、Ismet Ara

  DOI：10.14233/ajchem.2015.18896

  日期：——

  A series of nifuroxazide analogues [(2a-2e)-(10a-10f)] have been synthesized, structurally identified and tested for antimicrobial activity against a panel of bacteria (Gram-positive and Gram-negative) and the yeast-like pathogenic fungus Candida albicans. The most active compound in this series was 4-amino-benzoic acid (5-nitro-furan-2-ylmethylene)-hydrazide (2b) and 2-amino-benzoic acid (5-nitro-furan-2-ylmethylene)-hydrazide (2d). Furthermore, compounds (9a-9g) and (10a-10g) recorded no activity against selected species except compounds (9f) and (10f) suggesting that using furoic hydrazide and the corresponding hydrazide of thiophene did not improve the antimicrobial activities for this type of compounds. Regarding the activity against Candida albicans, all compounds showed no activity with an exception of substituted nitro furan (2a-2d).

  一系列硝呋醛酰肼类衍生物[(2a-2e)-(10a-10f)]已被合成、结构鉴定，并测试了其对一组细菌（革兰氏阳性和革兰氏阴性）和类酵母致病真菌白色念珠菌的抗微生物活性。在这一系列化合物中，活性最高的为4-氨基苯甲酸（5-硝基呋喃-2-亚甲基）酰肼（2b）和2-氨基苯甲酸（5-硝基呋喃-2-亚甲基）酰肼（2d）。此外，化合物（9a-9g）和（10a-10g）对选定物种无活性，除了化合物（9f）和（10f），这表明使用呋喃酰肼及其对应的噻吩酰肼并未提高此类化合物的抗菌活性。对于对白色念珠菌的活性，所有化合物均无活性，除了取代的硝基呋喃（2a-2d）。
• Eco-friendly synthesis, spectral and computational study of pyrrole-2-carboxaldehyde salicylhydrazone (PCSH) for its application
  作者：Poonam Rawat、R.N. Singh

  DOI：10.1016/j.molstruc.2015.07.005

  日期：2015.11

  Abstract In this paper we present eco-friendly synthesis of Pyrrole-2-carboxaldehyde salicylhydrazone (PCSH) and its molecular structural elucidation, spectral analysis and reactivity evaluation. Pyrrole-2-carboxaldehyde and salicyl hydrazide in water undergo condensation reaction to produce PCSH in good yield (88%). All results of quantum chemical calculation corroborate well with the experimental findings

  摘要 在本文中，我们介绍了吡咯-2-甲醛水杨腙（PCSH）的环保合成及其分子结构解析、光谱分析和反应性评价。Pyrrole-2-carboxaldehyde 和水杨酰肼在水中进行缩合反应，以良好的收率 (88%) 生成 PCSH。量子化学计算的所有结果都很好地证实了实验结果。PCSH 已通过元素分析、FT-IR、1 H NMR、UV-可见光和 ESI-质谱法进行表征。通过使用标准基组 6–31 + g (d, p) 和附加基组 6D 和 10F 执行 B3LYP 泛函，对 PCSH 进行了密度泛函理论 (DFT) 计算。已在二面角 N1C5C6N7 周围观察到 PCSH 的两个最稳定的构象异构体。在 FT-IR 光谱中的 O-H 伸缩振动中观察到的红移表明存在分子内氢键。发现 syn-syn（闭合）syn-syn（开放）之间的旋转势垒为 2966.9 kcal/mol。在实验 1 H NMR
• SYNTHESIS AND CHARACTERIZATION OF ANTIBACTERIAL Co(II), Cu(II), Ni(II), AND Zn(II) COMPLEXES OF ACYLHYDRAZINE DERIVED PYRROLYL COMPOUNDS
  作者：Zahid H. Chohan、Humayun Pervez、S. Kausar、Claudiu T. Supuran

  DOI：10.1081/sim-120003793

  日期：2002.4.29

  Acythydrazine derived pyrrolyl ligands and their metal [Co(II), Cu(II), Ni(II), and Zn(II)] complexes have been prepared and characterized on the basis of elemental analyses, magnetic moments, molar conductances and spectroscopic (electronic, IR, H-1 and C-13 NMR) data. All of these compounds function as tridentate ligands, with their deprotonated enolic form being preferred in the coordination to the metal ions. The title synthesized ligands and their metal(II) complexes have been screened for bactericidal activity against the pathogenic bacterial species Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, and it is shown that the metal complexes act as more active antibacterial agents than the uncomplexed ligands from which they derive.