5-chlorosalicylaldehyde isonicotinoyl hydrazone | 732-92-3

• 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: 5-chlorosalicylaldehyde isonicotinoyl hydrazone
• 英文别名: 5-chlorosalicylideneisonicotinoylhydrazine；isonicotinic acid-(5-chloro-2-hydroxy-benzylidenehydrazide)；H2Cinh；Isonicotinsaeure-(5-chlor-2-hydroxy-benzylidenhydrazid)；N-Isonicotinoyl-N'-(5-chlor-2-hydroxy-benzyliden)-hydrazin；2-Hydroxy-5-chlor-benzaldehyd-isonicotinoylhydrazon；N-[(5-chloro-2-hydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 732-92-3
• 化学式: C₁₃H₁₀ClN₃O₂
• mdl: MFCD00429564
• 分子量: 275.694
• InChiKey: XBMCOYHOYXSRDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chlorosalicylaldehyde isonicotinoyl hydrazone 在 乙酸酐 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 4-chloro-2-(5-pyridin-4-yl[1,3,4]oxadiazol-2-yl)phenol
  参考文献：
  名称：

  Heteroleptic binuclear copper(I) complexes bearing bis(salicylidene)hydrazone ligands: Synthesis, crystal structure and application in catalytic N-alkylation of amines

  摘要：

  A new series of heteroleptic binuclear Cu(I) bis(salicylidene)hydrazone complexes (1-4) bearing triphenylphospine coligands have been synthesized from the reactions of copper(II) precursor complex [CuCl2(PPh3)(2)] with oxadiazole compounds A-D, respectively. It has been observed that the oxadiazole compounds u ndergo ring cleavage with in situ reduction of Cu(II) ion, during the formation of complexes (1-4). The oxadiazoles (A-D) and the Cu(I) complexes (1-4) have been characterized by analytical and spectroscopic methods. Single crystal X-ray diffraction study of complex 2 has revealed a distorted tetrahedral geometry around each Cu(I) center. Catalytic efficiency of the new complexes on the N-alkylation of amines using alcohols was studied under optimized conditions. The new complexes have also been tested for their catalytic activity towards the direct N-alkylation of 2-nitropyridine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.12.015
• 作为产物：
  描述：

  异烟酸 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 5-chlorosalicylaldehyde isonicotinoyl hydrazone
  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

• Ruthenium(II) hydrazone Schiff base complexes: Synthesis, spectral study and catalytic applications
  作者：R. Manikandan、P. Viswanathamurthi、M. Muthukumar

  DOI：10.1016/j.saa.2011.08.033

  日期：2011.12

  Ruthenium(II) hydrazone Schiff base complexes of the type [RuCl(CO)(B)(L)] (were B=PPh(3), AsPh(3) or Py; L=hydrazone Schiff base ligands) were synthesized from the reactions of hydrazone Schiff base ligand (obtained from isonicotinoylhydrazide and different hydroxy aldehydes) with [RuHCl(CO)(EPh(3))(2)(B)] (where E=P or As; B=PPh(3), AsPh(3) or Py) in 1:1 molar ratio. All the new complexes have been

  [RuCl（CO）（B）（L）]类型的the（II）席夫碱配合物（是B = PPh（3），AsPh（3）或Py； L = hydr席夫碱配体）是由Sch席夫碱配体（由异烟酰酰肼和不同的羟基醛制得）与[RuHCl（CO）（EPh（3））（2）（B）]（其中E = P或As； B = PPh（3），AsPh）反应（3）或Py）的摩尔比为1：1。所有新的配合物均已通过分析和光谱（FT-IR，电子，（1）H，（13）C和（31）P NMR）数据进行了表征。暂时为它们分配了八面体结构。在存在N-甲基吗啉N-氧化物（NMO）作为助氧化剂的情况下，合成的配合物具有催化活性，可将苄醇氧化为苯甲醛，将环己醇氧化为环己酮。
• Organotin(IV) complexes derived from hydrazone Schiff base: Synthesis, crystal structure, in vitro cytotoxicity and DNA/BSA interactions
  作者：Kai Liu、Hun Yan、Guoliang Chang、Zhen Li、Meiju Niu、Min Hong

  DOI：10.1016/j.ica.2017.05.017

  日期：2017.8

  Abstract Four new organotin(IV) complexes Me 2 SnL 1 , Ph 2 SnL 1 , Me 2 SnL 2 and Ph 2 SnL 2 (H 2 L 1 = 5-chlorosalicylaldehyde isonicotinoyl hydrazone and H 2 L 2 = 2-hydroxy-4-methoxybenzaldehyde isonicotinoyl hydrazone) have been synthesized and characterized by elemental analyses, FT-IR, NMR ( 1 H, 13 C and 119 Sn) and single crystal X-ray diffraction techniques. The crystal structure analysis

  摘要四种新的有机锡（IV）配合物Me 2 SnL 1，Ph 2 SnL 1，Me 2 SnL 2和Ph 2 SnL 2（H 2 L 1 = 5-氯水杨醛异烟酰yl，H 2 L 2 = 2-羟基-4-已合成并通过元素分析，FT-IR，NMR（1 H，13 C和119 Sn）和单晶X射线衍射技术表征了甲氧基苯甲醛异烟酰characterized。晶体结构分析表明，配合物1和2为三核化合物，其中烯醇olic Sc​​hiff碱配体以ONO三齿模式螯合至锡中心。相比之下，配合物3和4是单核化合物，中心Sn原子采用五配位扭曲的三角双锥几何形状。通过MTT测定法研究了四种复合物对两种人类癌细胞系（A549和HeLa）的细胞毒性。结果表明这四种复合物表现出良好的抗癌活性，并且发现单核复合物4对HeLa癌细胞更有效。使用各种光谱技术研究了所有复合物与小牛胸腺DNA（CT-DNA）和牛血清白蛋白（BSA）之间的相互作用。粘度测量，热温度（T
• Synthesis and X-Ray Structural Characterization of Dioxomolybdenum(VI) Complexes with 2’-(5-Chloro-2-hydroxybenzylidene)isonicotinohydrazide and 2’-(2-Hydroxy-3-methoxybenzylidene)isonicotinohydrazide
  作者：Yan Lei、Chuan Fu

  DOI：10.1080/15533174.2011.568465

  日期：2011.7.1

  788(3), γ = 75.072(3)°, V = 813.6(5) Å3, Z = 2, R 1 = 0.0291, wR 2 = 0.0617, S = 1.044. The crystal of (2) crystallizes in monoclinic space group P21/n, with a = 6.792(2), b = 30.259(4), c = 7.920(3) Å, β = 93.703(3)°, V = 1624.3(8) Å3, Z = 4, R 1 = 0.0501, wR 2 = 0.1250, S = 1.087. X-ray analysis indicates that the structures of both complexes are similar to each other. The molybdenum atom in each complex

  两个新的二氧钼钼（VI）配合物，[MoO 2（Cinh）（CH 3 OH）]（1）和[MoO 2（Minh）（CH 3 OH）]（2），以及异烟肼hydr配体H 2 Cinh和H 2分别从异烟肼和5-氯水杨醛和3-甲氧水杨醛衍生的Minh已合成，并通过理化方法和单晶X射线测定对其结构进行了表征。（1）的晶体在三斜晶空间群P -1中结晶，a = 6.553（2），b = 10.737（4），c = 12.907（4）Å，α = 68.021（2），β = 83.788（3 ），γ＝ 75.072（3）°，V＝ 813.6（5）3，Z＝ 2，R 1＝ 0.0291，wR 2＝ 0.0617，S＝ 1.044。（2）在晶体结晶在单斜晶系空间群P 2 1 / Ñ，具有一个= 6.792（2），b = 30.259（4），C ^ = 7.920（3）埃，β = 93.703（3）°，V = 1624
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——
• Ruthenium(II) bis(hydrazone) complexes derived from 1,3,4-oxadiazoles: Synthesis, crystal structure and catalytic application in N-alkylation reactions
  作者：Govindan Prakash、Rangasamy Ramachandran、Muthukumaran Nirmala、Periasamy Viswanathamurthi、Jesus Sanmartin

  DOI：10.1016/j.ica.2015.01.002

  日期：2015.3

  1,3,4-Oxadiazoles (A-C) were derived via a series of reactions between isoniazid and salicylaldehydes. While reacting the oxadiazoles with [RuHCl(CO)(PPh3)(3)] in the presence of NaOH, mononuclear ruthenium(II) complexes bearing 'salen' type N,N'-bis(salicylidene) hydrazone ligands (1-3) were obtained. The oxadiazoles and ruthenium(II) complexes were characterized by analytical and spectral methods. The single crystal XRD analyses of complexes 1 and 2 suggested an octahedral geometry around ruthenium(II) ions in which the bis(hydrazone) act as mononegative bidentate ligands. It was also observed that the presence of an intramolecular hydrogen bonding between the hydroxyl proton and one of the azomethine nitrogens in all the complexes. Further, the complexes were proved as versatile catalysts for the N-alkylation of amines with alcohols under optimized reaction conditions. (C) 2015 Elsevier B.V. All rights reserved.