2-pyridinecarbaldehyde isonicotinoylhydrazone | 15017-32-0

• 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: 2-pyridinecarbaldehyde isonicotinoylhydrazone
• 英文别名: N’-(pyridin-2-ylmethylene)isonicotinohydrazide；N-(pyridin-2-ylmethylideneamino)pyridine-4-carboxamide
• CAS: 15017-32-0
• 化学式: C₁₂H₁₀N₄O
• mdl: MFCD00446451
• 分子量: 226.238
• InChiKey: WRHZTTISLCLBBE-UHFFFAOYSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  2-pyridinecarbaldehyde isonicotinoylhydrazone 在 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以92%的产率得到2-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridine
  参考文献：
  名称：

  Preparation and Acetylcholinesterase Inhibitory Activities of Pyridine-Based 1,3,4-Oxadiazole Derivatives

  摘要：

  DOI：

  10.3987/com-20-14266
• 作为产物：
  描述：

  异烟酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 2-pyridinecarbaldehyde isonicotinoylhydrazone
  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

• Hydrazone chelators for the treatment of iron overload disorders: iron coordination chemistry and biological activity
  作者：Paul V. Bernhardt、Piao Chin、Philip C. Sharpe、Des R. Richardson

  DOI：10.1039/b704102k

  日期：——

  number of the HPCIH analogues show high activity at inducing Fe efflux from cells and also at preventing Fe uptake by cells from the serum Fe transport protein transferrin. As a class of ligands, these chelators are more effective at reducing Fe uptake from transferrin than inducing Fe mobilisation from cells. This may be related to their ability to intercept Fe(II) after its release from transferrin within

  潜在的三齿配体2-吡啶甲醛异烟酰yl（HPCIH）及其类似物是一类新兴的口服有效铁螯合剂，对治疗铁超载疾病显示出巨大的希望。本文中，我们对HPCIH类似物的Fe配位化学进行了广泛的研究，包括这些螯合剂的第一个晶体学表征的Fe（II）配合物。与大多数其他临床上有效的铁螯合剂不同，HPCIH类似物结合Fe（II）而不结合Fe（III）。实际上，这些螯合剂形成低旋转双配体Fe（II）配合物，尽管NMR表明该配合物接近高旋转/低旋转交叉。所有的Fe配合物都显示出高电位的Fe（III / II）氧化还原对（> 500 mV vs. NHE）和在水性或混合的水性/有机溶剂中的循环伏安法是不可逆的，因为在氧化时会发生快速水合反应。许多HPCIH类似物在诱导Fe从细胞中流出以及防止细胞从血清Fe转运蛋白转铁蛋白中吸收Fe方面显示出很高的活性。作为一类配体，这些螯合剂在减少铁从转铁蛋白中摄取比诱导从细胞中动
• A Photoluminescent zig-zag 1D Coordination Polymer with Mixed Ligands [Zn(absa)(pcih)](CH₃OH)
  作者：Dong-Qing Li、Xing Liu、Jian Zhou

  DOI：10.1515/znb-2008-1115

  日期：2008.11.1

  A novel 1D zinc(II) coordination polymer [Zn(absa)- (pcih)](CH₃OH) (1) (Habsa = 4-aminobenzenesulfonic acid, Hpcih = 2-pyridinecarbaldehyde isonicotinoylhydrazone) has been synthesized by solvothermal reaction at 72 °C and structurally characterized. Each Zn²⁺ ion is five-coordinated by three N atoms and one O atom from two pcih ligands, and one O atom of an absa ligand, forming a distorted squarepyramidal geometry. Zn²⁺ ions are bridged by pcih ligands in a zig-zag arrangement generating infinite chains with appended absa ligands. Photoluminescent studies have shown that 1 exhibits an emission at 535 nm (λ_ex = 492 nm).

  摘要：已合成一种新型的1D锌(II)配位聚合物[Zn(absa)-(pcih)](CH3OH) (1) (Habsa = 4-氨基苯磺酸，Hpcih = 2-吡啶甲醛异烟肼酰脒)通过72°C的溶剂热反应合成并进行了结构表征。每个Zn2+离子由两个pcih配体的三个N原子和一个O原子以及一个absa配体的一个O原子五配位，形成畸变的方锥形几何结构。Zn2+离子由pcih配体以锯齿状排列桥接，生成具有附加absa配体的无限链。光致发光研究表明1在535 nm处发射（λex = 492 nm）。
• Synthesis, Crystal Structures, Characterization and Catalytic Property of Manganese(II) Complexes Derived from Hydrazone Ligands
  作者：Yao Tan

  DOI：10.17344/acsi.2020.6136

  日期：——

  manganese(II) complex [MnL 1 Br 2 (OH 2 )] ( 1 ), and a new nitrato-coordinated mononuclear manganese(II) complex [Mn(L 2 ) 2 (ONO 2 )(OH 2 )]NO 3 ( 2 ), with the hydrazone ligands 4-hydroxy- N’ -(pyridin-2-ylmethylene)benzohydrazide (HL 1 ) and N’ -(pyridin-2-ylmethylene)isonicotinohydrazide (HL 2 ), have been synthesized and structurally characterized by physico-chemical methods and single crystal X-ray

  一种新型的溴配位单核锰（II）配合物[MnL 1 Br 2（OH 2）]（1）和一种新型的硝酸根配位单核锰（II）配合物[Mn（L 2）2（ONO 2）（OH） 2）] NO 3（2）与配体4-羟基-N'-（吡啶-2-基亚甲基）苯并酰肼（HL 1）和N'-（吡啶-2-基亚甲基）异烟酰肼（HL 2）具有通过物理化学方法和单晶X射线测定合成并在结构上进行了表征。单晶结构分析表明，配合物1中的Mn原子为八面体配位，而配合物2中的Mn原子为五角双锥体配位。评价了配合物对苯乙烯环氧化的催化性能。
• Biological Properties of Heterocyclic Pyridinylimines and Pyridinylhydrazones
  作者：Francislene J. Martins、Rebeca Mol Lima、Juliana Alves dos Santos、Patricia de Almeida Machado、Elaine Soares Coimbra、Adilson David da Silva、Nádia Rezende Barbosa Raposo

  DOI：10.2174/1570180812666141216205601

  日期：2015.10.30

  This work describes the synthesis and biological properties of a series of 2- and 4- pyridinylimines and pyridinylhydrazones. All compounds were evaluated in vitro against two species of Leishmania. The antioxidant activity and the toxic effect against murine peritoneal macrophages of the compounds were also performed. The synthesized compounds showed significant antileishmanial and antioxidant activities. For the antileishmanial assay, compounds 1a, 1d and 2a were active against the Leishmania species, and compound 2a was the most effective on promastigotes (IC50 value = 3.38 µM) and amastigotes (IC50 value = 18.96 µM) of L. amazonensis. Only compound 2a exhibited toxicity against murine peritoneal macrophages (CC50 of 54.35 µM). However, this compound was 2.8 times more destructive to the intracellular amastigotes than the host cell. Regarding the antioxidant activity, compounds 1a and 2a exhibited a strong antioxidant effect (IC50 values of 8.79 µM and 19.82 µM), compound 1a being better than the L-ascorbic acid (9.48 µM), used as reference.

  本研究介绍了一系列 2-和 4-吡啶亚胺及吡啶肼的合成及其生物学特性。所有化合物都针对两种利什曼原虫进行了体外评估。此外，还对这些化合物的抗氧化活性和对小鼠腹腔巨噬细胞的毒性作用进行了评估。合成的化合物显示出显著的抗利什曼病和抗氧化活性。在抗利什曼病菌试验中，化合物 1a、1d 和 2a 对利什曼病菌具有活性，其中化合物 2a 对亚马逊利什曼原虫（IC50 值 = 3.38 µM）和非原虫（IC50 值 = 18.96 µM）最为有效。只有化合物 2a 对小鼠腹腔巨噬细胞表现出毒性（CC50 为 54.35 µM）。不过，这种化合物对细胞内母细胞的破坏力是宿主细胞的 2.8 倍。在抗氧化活性方面，化合物 1a 和 2a 表现出很强的抗氧化效果（IC50 值分别为 8.79 µM 和 19.82 µM），化合物 1a 的抗氧化效果优于作为参考的 L-抗坏血酸（9.48 µM）。
• Synthesis, structural characterization, and molecular docking studies of bioactive bismuth(III) complexes with substituted hydrazones
  作者：Sumaira Abbas、Imtiaz-ud-Din、Mehwish Mehmood、M. Khawar Rauf、S. Sikander Azam、Ihsan-ul Haq、M. Nawaz Tahir、Nousheen Parvaiz

  DOI：10.1016/j.molstruc.2021.129870

  日期：2021.4

  4-hydroxybenzhydrazide, thiophene-2-carboxylic acid hydrazide, 3-hydroxy-2-naphthoic acid hydrazide, Isonicotic acid hydrazide and appropriate aromatic aldehydes like pridine-2-carboxaldehyde and quinoline-2-carboxyaldehyde. These hydrazones (ligands),then complexed to Bi(III) species to yield the target compounds. They were characterized by FTIR, and NMR spectroscopy to find out an explicit evidence about

  具有通式的八种取代的新的铋（III）配合物（1-8）；[Bi（RCONHNCHC 5 H 4 N）Cl x ]和[Bi（RCONHNCHC 9 H 6 N）Cl x ]，其中R = C 10 H 7 O （1，和8），C 4 H 3 S （2）， C 6 H 5 O （3和6）， C 7 H 7 （4）， C 5 H 4 N （5和7），已经准备好x = 2或3。取代的腙（我1 -I 8）是由化学计量的量的各酰肼如对甲酰肼的反应来合成，4- hydroxybenzhydrazide，噻吩-2-羧酸酰肼，3-羟基-2-萘甲酸酰肼，异氰酸酰肼和合适的芳族醛，如吡啶-2-羧醛和喹啉-2-羧醛。然后将这些（配体）与Bi（III）物种络合，生成目标化合物。通过FTIR和NMR光谱对它们进行了表征，以找到有关其结构基序的明确证据。（1＆I 6）的X射线数据进一步验证合成化合物的化学结构。（1）的分子几