N'-(pyridin-2-ylmethylene)picolinohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N'-(pyridin-2-ylmethylene)picolinohydrazide
• 英文别名: N'-(1-(pyridin-2-yl)ethylidene)picolinohydrazide；2-pyridine picolyl hydrazone；N′-(pyridin-2-ylmethylene)picolinohydrazide；N’-(pyridin-2-ylmethylene)picolinohydrazide；2-pyridinecarbaldehyde picolinoyl hydrazone；N-(pyridin-2-ylmethylideneamino)pyridine-2-carboxamide
• 化学式: C₁₂H₁₀N₄O
• 分子量: 226.238
• InChiKey: GMGRADYVFCNBHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(pyridin-2-ylmethylene)picolinohydrazide 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  dra和钯配合物在固态和溶液中的配位结构转化

  摘要：

  我们制备的腙-钯（II）配合物[的PdCl 2（HL Ñ）]和[的PdCl（L Ñ）]（Ñ = 1-3）由反应[的PdCl 2（COD）]或[的PdCl 2（PHCN ）2 ]和HL n { N ′-（吡啶-2-基亚甲基）吡啶甲酸酰肼（HL 1），N ′-[1-（吡啶-2-基）亚乙基]吡啶甲酸酰肼（HL 2）和N的the配体′-[（（6-甲基吡啶-2-基）亚甲基]吡啶并酰肼（HL 3）}。配合物的结构通过X射线分析确定。有κ腙配体Ñ（PY1），κÑ（亚胺）和κ Ñ（酰胺化），κ Ñ在（PY2）的二齿配位方式[的PdCl 2（HL Ñ）]（1，Ñ = 1; 2，Ñ = 2）和在[的PdCl 2（HL 3） ]（3）。与此相反，κ的三齿配位方式Ñ（PY1），κ Ñ（亚胺），κ Ñ（PY2）和κ Ñ（PY1），κ Ñ（酰胺化），κ Ñ（PY2）在[的PdCl（L观察Ñ）]（4，n = 1; 5，n

  DOI：

  10.1021/acs.inorgchem.5b01128
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N'-(pyridin-2-ylmethylene)picolinohydrazide
  参考文献：
  名称：

  Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

  摘要：

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.040

文献信息

• The role of unconventional stacking interactions in the supramolecular assemblies of Hg(<scp>ii</scp>) coordination compounds
  作者：Ghodrat Mahmoudi、Antonio Bauzá、Atash V. Gurbanov、Fedor I. Zubkov、Waldemar Maniukiewicz、Antonio Rodríguez-Diéguez、Elena López-Torres、Antonio Frontera

  DOI：10.1039/c6ce02073a

  日期：——

  (HS) analyses were employed to gain additional insight into interactions responsible for the packing of complexes 1–9. Quantitative examination of 2D fingerprint plots revealed, among others, the dominating participation of H⋯H and H⋯X interactions in the molecular packing. Moreover, C–H⋯X hydrogen bonds, π–π, and chelate-ring–π interactions are described and analysed by means of density functional theory

  在这项研究中，九种汞（II）配合物的组成为[Hg（L n）（X）2 ]（X = Cl，Br和I，n = 1-3），（L 1 = 2-吡啶吡啶甲基hydr） ; 合成L 2＝（2-乙酰吡啶吡啶甲基on）和L 3＝（2-苯基吡啶吡啶甲基）并进行光谱表征。X射线单晶晶体学分析表明，根据与金属中心配位的阴离子，分子络合物可以聚集成更大的实体。此外，使用Hirshfeld表面（HS）分析来进一步了解负责配合物1–9堆积的相互作用。二维指纹图谱的定量检查显示，除其他外，H⋯H和H⋯X相互作用在分子包装中的主要参与。此外，通过密度泛函理论（DFT）计算来描述和分析C–H⋯X氢键，π–π和螯合环–π相互作用，因为它们在三维超分子构架的构建中起着重要作用。还研究了卤化物对组件能量特征的影响。
• Iron catalysed assembly of an asymmetric mixed-ligand triple helicate
  作者：Paul V. Bernhardt、Piao Chin、Des R. Richardson

  DOI：10.1039/b408781j

  日期：——

  The 2-pyridinecarbaldehyde isonicotinoyl hydrazone (HPCIH) family of ligands are typically tridentate N,N,O chelators that exhibit very high in vitro activity in mobilizing intracellular Fe and are promising candidates for the treatment of Fe overload diseases. Complexation of ferrous perchlorate with HPCIH in MeCN solution gives the expected six-coordinate complex FeII(PCIH)2. However, complexation of FeII with 2-pyridinecarbaldehyde picolinoyl hydrazone (HPCPH, an isomer of HPCIH) under the same conditions leads to spontaneous assembly of an unprecedented asymmetric, mixed-ligand dinuclear triple helical complex FeII2(PCPH)2(PPH), where PPH2− is the dianion of bis(picolinoyl)hydrazine. The X-ray crystal structure of this complex shows that each ligand binds simultaneously to both metal centres in a bidentate fashion. The dinuclear complex exhibits two well separated and totally reversible FeIII/II redox couples as shown by cyclic voltammetry in MeCN solution.

  2-pyridinecarbaldehyde isonicotinoyl hydrazone (HPCIH) 配体家族是典型的三叉N,N,O螯合剂，在体外调动细胞内铁元素方面表现出极高的活性，是治疗铁超载疾病的理想候选配体。高氯酸亚铁与 HPCIH 在 MeCN 溶液中络合，可得到预期的六配位络合物 FeII(PCIH)2。然而，在相同条件下，FeII 与 2-吡啶甲醛吡啶酰腙（HPCPH，HPCIH 的异构体）络合时，会自发形成一种前所未有的不对称、混合配体的双核三螺旋络合物 FeII2(PCPH)2(PPH)，其中 PPH2- 是双（吡啶酰）肼的二元离子。该复合物的 X 射线晶体结构显示，每个配体都以双齿方式同时与两个金属中心结合。在 MeCN 溶液中的循环伏安法显示，该双核复合物具有两个完全分离且完全可逆的 FeIII/II 氧化还原偶。
• Supramolecular lead(<scp>ii</scp>) architectures engineered by tetrel bonds
  作者：Farhad Akbari Afkhami、Ghodrat Mahmoudi、Fengrui Qu、Arunava Gupta、Muhammet Köse、Ennio Zangrando、Fedor I. Zubkov、Ibon Alkorta、Damir A. Safin

  DOI：10.1039/d0ce00102c

  日期：——

  The structures, including tetrel bonding, of Pb^II coordination compounds assembled from N′-(pyridin-2-ylmethylene)picolinohydrazide, N′-(pyridin-2-ylmethylene)nicotinohydrazide and N′-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide ligands are discussed.

  讨论了由N'-（吡啶-2-基亚甲基）吡啶酮肼，N'-（吡啶-2-基亚甲基）烟酰肼和N'-（1-（吡啶-2-基）乙烯基）异烟酰肼配体组装的Pb^II配位化合物的结构，包括四元键合。
• Synthesis, Crystal Structures and Urease Inhibition of Mononuclear Copper(II) and Nickel(
  作者：Jian Jiang、Peng Liang、Huiyuan Yu、Zhonglu You

  DOI：10.17344/acsi.2022.7513

  日期：——

  Three mononuclear copper(II) and nickel(II) complexes, [Cu(L1)(NCS)(CH3OH)] (1), [Cu(L2)(NCS)] (2) and [Ni(L2)(N3)] (3), where L1 and L2 are the monoanionic forms of the Schiff bases N'-(pyridin-2-ylmethylene)picolinohydrazide (HL1) and 4-methyl-2-(((pyridin-2-ylmethyl)imino)methyl)phenol (HL2), have been prepared and characterized by elemental analysis, IR and UV-Vis spectroscopy, as well as single

  三种单核铜 (II) 和镍 (II) 配合物，[Cu(L1)(NCS)(CH3OH)] (1)、[Cu(L2)(NCS)] (2) 和 [Ni(L2)(N3) ] (3)，其中 L1 和 L2 是席夫碱 N'-(pyridin-2-ylmethylene)picolinohydrazide (HL1) 和 4-methyl-2-(((pyridin-2-ylmethyl)imino)methyl 的单阴离子形式)苯酚 (HL2)，已通过元素分析、IR 和 UV-Vis 光谱以及单晶 X 射线衍射研究进行了制备和表征。配合物1中的Cu原子呈方锥配位，与配体L的三个N原子和硫氰酸盐配体的N原子在基面，与甲醇O原子在顶端。配合物 2 和 3 中的 Cu 和 Ni 原子与席夫碱配体的三个供体原子以及硫氰酸盐和叠氮化物配体的末端 N 原子呈方形平面配位。复合物 1 和 2 抑制杰克豆脲酶，IC50 值分别为
• Preparations, characterization, and biological features of mononuclear Cu(II) complexes based on hydrazone ligands
  作者：Jie Qin、Shan-Shan Zhao、Ya-Ping Liu、Zhong-Wei Man、Peng Wang、Li-Na Wang、Yu Xu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2016.09.015

  日期：2016.10

  Cu(HL2)Cl2 (2), and Cu(L3)SCN (3) have been synthesized based on chelating hydrazone ligands HL1, HL2, and HL3, respectively. These new compounds gave satisfactory IR-spectroscopic data and were further characterized by elemental and X-ray diffraction analyses. Their urease inhibitory evaluation was tested in vitro against jack bean urease. The results showed that the inhibitory activities of the copper

  基于che配体HL 1的螯合，合成了三种单核Cu（II）配合物Cu（HL 1）Cl 2（1），Cu（HL 2）Cl 2（2）和Cu（L 3）SCN（3）。HL 2和HL 3。这些新化合物提供了令人满意的红外光谱数据，并通过元素和X射线衍射分析进一步表征。他们对脲酶的抑制性评估在体外针对千斤顶进行了测试脲酶。结果表明，铜配合物的抑制活性均优于阳性对照。进行了酶动力学研究以估计铜络合物的抑制机理。已经进行了分子对接模拟以使它们的结合模型合理化。此外，还研究了它们与血清白蛋白的相互作用。