pyrazole-3,5-dicarbohydrazide | 952101-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: pyrazole-3,5-dicarbohydrazide
• 英文别名: 1h-Pyrazole-3,5-dicarbohydrazide；1H-pyrazole-3,5-dicarbohydrazide
• CAS: 952101-18-7
• 化学式: C₅H₈N₆O₂
• 分子量: 184.158
• InChiKey: XOAXKUJQRYTQRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pyrazole-3,5-dicarbohydrazide 在 氨 作用下， 以 乙醇 为溶剂， 反应 8.5h， 生成 C₂₇H₂₅ClN₆O₈Zn₂*3H₂O
  参考文献：
  名称：

  吡唑桥联的六齿区室配体的第一排晚期过渡金属配合物：合成，表征，抗菌活性和DNA结合/裂解研究

  摘要：

  已经制备了一系列具有μ-1,2二嗪桥联的双核Co II，Ni II，Cu II和Zn II配合物，并通过各种物理化学方法对其进行了表征。六齿配体是通过将吡唑-3,5-二乙酰肼与2-羟基萘醛（LH 3）以1：2的比例缩合而合成的。发现所有配合物本质上都是具有八面体几何形状的单体，并且可以作为非电解质。筛选配体和复合物对大肠杆菌的抗菌活性并使其与DNA相互作用，以通过吸收，流体动力学，热变性和电泳研究来研究其结合/裂解能力。结果预测了插入结合模式。凝胶电泳数据表明配体和复合物都在更大程度上切割了DNA。

  DOI：

  10.1007/s00044-012-0199-3
• 作为产物：
  描述：

  1H-吡唑-3,5-二甲酰氯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 96.0h， 生成 pyrazole-3,5-dicarbohydrazide
  参考文献：
  名称：

  Versatility in the coordination behavior of a hexatopic compartmental Schiff-base ligand in the architecture of binuclear transition metal(II) complexes

  摘要：

  Condensation of 1H-pyrazole-3,5-dicarboxylic hydrazide with 1H-indole-2,3-dione (isatin) yield the compartmental ligand, which is capable of encapsulating two transition metal ions namely CoII, NiII, CuII, and ZnII. The ligand is a binuclear hexadentate chelate with N4O2 donating sites. The pyrazole core provides the diazine fragment, which serves as an endogenous bridge between the two metal centers. In CoII and NiII complexes, the ligand is in the imidol form and the subsequent coordination through the imidol oxygen. In other complexes, the lactonic oxygen takes part in ligation. All the complexes are non-electrolytes and soluble in DMSO, DMF, and acetonitrile. Spectral and magnetic studies along with analytical data suggest octahedral geometry for the CoII and NiII complexes, whereas the CuII and ZnII complexes are assigned square pyramidal geometry. The CuII and NiII complexes show one electron redox behavior and the rest are electrochemically inactive.

  DOI：

  10.1080/00958971003802075

文献信息

• Self assembled tetranuclear Cu4(ii), Ni4(ii) [2 × 2] square grids and a dicopper(ii) complex of heterocycle based polytopic ligands - Magnetic studies
  作者：Tarak Nath Mandal、Somnath Roy、Saugata Konar、Atanu Jana、Sangita Ray、Kinsuk Das、Rajat Saha、Mohamed Salah El Fallah、Ray J. Butcher、Sudipta Chatterjee、Susanta Kumar Kar

  DOI：10.1039/c1dt10813a

  日期：——

  1229) self-assemble to form homoleptic [2 × 2] tetranuclear M4 (M = Cu(II) and Ni(II)) square grids structures [Cu4(PyPzOAP)4](NO3)4 (1), [Cu4(PzOAP)4](ClO4)4 (2) and [Ni4(PyPzOAP)4](NO3)4·8H2O·2CH3CN (3). While the ligand 2-PzCAP forms a dicopper(II) complex [Cu2(2-PzCAP)(OH)(NO3)(H2O)](NO3)·2H2O (4). The complex 1 is a perfect square grid (a = 4.201 Å), whereas, 2 and 3 are almost square grids. All

  对位配体PyPzOAP（N -[（Z）-氨基（吡啶-2-基）亚甲基] -5-甲基-1-（吡啶-2-基）-1 H-吡唑-3-碳酰肼酸）和多配体2-PzCAP（Ñ ' 3，Ñ ' 5 -双[（1- ë）-1-（吡啶-2-基）亚乙基] -1- ħ吡唑-3,5- dicarbohydrazide）是通过亚氨基吡啶甲酸亚氨基甲酸甲酯与5-甲基-1-（2-吡啶基）吡唑-3-碳酰肼的缩合反应原位合成的。2-乙酰基吡啶 和 吡唑-3,5-二甲酰肼分别。配体PyPzOAP和PzOAP（先前报道，Dalton Trans。，2007，1229 ）自组装形成均相[2×2]四核M 4（M = Cu（II）和Ni（II））方形网格结构[Cu 4（PyPzOAP）4 ]（NO 3）4（1），[Cu 4（PzOAP）4 ]（ClO 4）4（2）和[Ni 4（PyPzOAP）4 ]（NO 3）4 ·8H 2 O·2CH 3
• Transition metal complexes of pyrazole head 24-membered polyazamacrocyclic bimetal cores: synthesis, characterization, electrochemistry and spectral study
  作者：Srinivasa Budagumpi、M. P. Sathisha、Naveen V. Kulkarni、Gurunath S. Kurdekar、Vidyanand K. Revankar

  DOI：10.1007/s10847-009-9649-z

  日期：2010.4

  A series of new 24-membered macrocyclic CoII, NiII, CuII and ZnII complexes of the ligands L1H2 and L2H2 were prepared by the non-template and template methods respectively. The ligand L1H2 was formed by the condensation of pyrazole-3,5-dicarbohydrazide and glyoxal and all attempts to isolate the ligand L2H2 were unsuccessful. These, ligand and transition metal complexes were characterized on the basis of elemental analysis, IR, 1HNMR, UV–Visible, magnetic susceptibility measurements, ESR, conductivity measurements, FAB-mass and thermal analysis. The redox behavior of metal ions in the polyazamacrocyclic ligand field is also studied. Electroreduction of carbon dioxide to carbon monoxide is mainly focused on using polydentate azamacrocyclic ligands with amine and imine functionalities, based on the electrochemical behavior of nickel (II) ion in the macrocyclic territory.

  通过非模板法和模板法分别制备了配体 L1H2 和 L2H2 的一系列新的 24 元大环 CoII、NiII、CuII 和 ZnII 配合物。配体 L1H2 由吡唑-3,5-二甲酰肼和乙二醛缩合而成，而分离配体 L2H2 的所有尝试均未成功。这些配体和过渡金属配合物的特征是基于元素分析、红外光谱、1HNMR、紫外-可见光谱、磁感应强度测量、ESR、电导率测量、FAB-质量和热分析。此外，还研究了金属离子在多氮杂环配体场中的氧化还原行为。根据镍（II）离子在大环领域中的电化学行为，二氧化碳电还原成一氧化碳的研究主要集中在使用具有胺和亚胺官能团的多齿偶氮杂环配体上。
• Synthesis and structure of transition metal complexes derived from a novel polynucleating oxaza macrocycle having diazine and phenoxo bridging components
  作者：Anupama Kamath、Vidyanand K. Revankar

  DOI：10.1007/s10847-011-9953-2

  日期：2012.2

  analysis. Present ZnII and CuII complexes are binuclear in nature with octahedral geometry, where as CoII and NiII complexes are tetranuclear with square-planar geometry. CuII and CoII complexes are paramagnetic whereas ZnII and NiII complexes are diamagnetic. Only the copper complex has shown redox property in the applied potential range while the ligand and other complexes are found to be electrochemically

  已经合成了衍生自 pyrazole-3,5-dicarbohydrazide 和 2,6-diformyl-4-methylphenol 的 2:2 缩合的多核恶氮大环配体 (LH4) 的新型 CoII、NiII、CuII 和 ZnII 配合物。配体和配合物在元素分析、IR、1HNMR、UV-可见光、磁化率、ESR 和电导率测量、FAB 质量和热分析的基础上进行了表征。目前的 ZnII 和 CuII 配合物本质上是具有八面体几何形状的双核，而 CoII 和 NiII 配合物是具有方形平面几何形状的四核。CuII 和 CoII 配合物是顺磁性的，而 ZnII 和 NiII 配合物是抗磁性的。只有铜配合物在施加的电位范围内显示出氧化还原特性，而发现配体和其他配合物在电化学上是无害的。
• Bis-(2-Hydroxybenzylidene)-1H-Pyrazole 3,5-Dicarbohydrazide as a Novel Chemosensor for the Detection of Endogenous Zinc: A Fluorometric Study
  作者：Krishna Naik、Vidyanand Revankar

  DOI：10.1007/s10895-018-2273-9

  日期：2018.9

  The study reports synthesis and photophysical studies of a new zinc sensing pyrazole scaffold structurally characterized to be bis(2-hydroxybenzylidene)-1H-pyrazole-3,5-dicarbohydrazide (PHSA). Excitation of the probe at 330 nm results in an emission band at 417 nm which ratiometrically red shifts to 466 nm upon Zn2+ addition in an unprecedented way. The photo induced electron transfer (PET) coupled intramolecular charge transfer (ICT) working for a dual-channel fluorescence emission pathway is observed and studies were supported with density functional theory and NMR titration experiments. The probe exhibited dissociation constant of 1.2156 and detection limit as low as 992 nM. The cytotoxic effects of the probe on 60 tumour cell lines were tested. The intracellular zinc sensing with reversible binding potential is verified with fluorescence microscopy experiment.

  该研究报告了一种新型锌传感吡唑支架的合成和光物理研究，其结构特征为双(2-羟基苯亚甲基)-1H-吡唑-3,5-二甲酸肼（PHSA）。探针在 330 nm 处受到激发，在 417 nm 处产生发射带，在加入 Zn2+ 后，发射带以前所未有的方式按比例红移到 466 nm 处。光诱导电子转移（PET）耦合分子内电荷转移（ICT）在双通道荧光发射途径中起作用，密度泛函理论和核磁共振滴定实验为研究提供了支持。该探针的解离常数为 1.2156，检测限低至 992 nM。该探针对 60 种肿瘤细胞系进行了细胞毒性效应测试。荧光显微镜实验验证了这种具有可逆结合电位的细胞内锌传感。
• Pyrazole bridged dinuclear Cu(II) and Zn(II) complexes as phosphatase models: Synthesis and activity
  作者：Krishna Naik、Anupama Nevrekar、Dhoolesh Gangaram Kokare、Avinash Kotian、Vinayak Kamat、Vidyanand K. Revankar

  DOI：10.1016/j.molstruc.2016.07.036

  日期：2016.12

  Abstract Present work describes synthesis of dibridged dinuclear [Cu 2 L 2 (μ 2 -NN pyr)(NO 3 ) 2 (H 2 O) 2 ] and [Zn 2 L(μ-OH)(μ-NNpyr)(H 2 O) 2 ] complexes derived from a pyrazole based ligand bis(2-hydroxy-3-methoxybenzylidene)-1H-pyrazole-3,5-dicarbohydrazide. The ligand shows dimeric chelate behaviour towards copper against monomeric for zinc counterpart. Spectroscopic evidences affirm octahedral

  摘要 目前的工作描述了双桥双核 [Cu 2 L 2 (μ 2 -NNpyr)(NO 3 ) 2 (H 2 O) 2 ] 和 [Zn 2 L(μ-OH)(μ-NNpyr)(H 2 O) 2 ] 衍生自基于吡唑的配体双(2-羟基-3-甲氧基亚苄基)-1H-吡唑-3,5-二碳酰肼的配合物。配体显示出对铜的二聚螯合行为，而锌对应物则显示出单体螯合行为。光谱证据证实溶液态金属离子周围的八面体环境和配合物的非电解性质。两种配合物都是磷酸单酯水解的活性催化剂，一级k cat 值在2×10 -3 s -1 的范围内。锌配合物对水解表现出良好的催化效率。双核复合物通过路易斯酸活化水解，