13025-99-5

Usage

Uses

Used in Pharmaceutical Industry:
N-[(E)-4-pyridylmethyleneamino]pyridine-4-carboxamide is used as a potential pharmaceutical compound for its possible interactions with biological systems. Its unique structure may allow it to be developed into a drug candidate for various therapeutic applications.
Used in Research and Development:
N-[(E)-4-pyridylmethyleneamino]pyridine-4-carboxamide is used as a research compound in the study of organic chemistry and drug development. Its properties and potential interactions with biological systems make it a valuable tool for scientists to explore new avenues in medicinal chemistry and drug discovery.

Upstream product

• 872-85-5 pyridine-4-carbaldehyde 
• 54-85-3 isoniazid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 
• 55-22-1 pyridine-4-carboxylic acid 

Relevant academic research and scientific papers

Isonicotinohydrazones as inhibitors of alkaline phosphatase and ecto-5′-nucleotidase

A series of isonicotinohydrazide derivatives was synthesized and tested against recombinant human and rat ecto-5′-nucleotidases (h-e5′NT and r-e5′NT) and alkaline phosphatase isozymes including both bovine tissue-non-specific alkaline phosphatase (b-TNAP)

Single Dynamic Covalent Bond Tailored Responsive Molecular Junctions

Responsive molecular devices are one of the core units for molecular electronics, and dynamic covalent bonds (DCBs) provide the opportunity for the fabrication of responsive molecular devices. Herein we employ a single dynamic acyl hydrazone bond to fabricate tailored molecular devices using the scanning tunneling microscopy break-junction technique (STM-BJ) and the eutectic Ga-In technique (EGaIn). We found that the single-DCB-tailored molecular devices exhibited acid-base and/or photo-thermal response with three well-defined molecular conductance states. The reversible switching has the ON/OFF ratio of ≈10 between each state for single-molecule junctions and ≈3 for the SAMs-based molecular junctions. Combined with the density functional theory calculations, we revealed that the multiple conductance states of these molecular junctions originate from the dynamic acyl hydrazone bond exchange and C=N isomerization. Our work opens the avenue towards the design of tailored single-molecule electrical devices by implanting dynamic covalent bonds in molecular architectures.

A novel dicationic ionic liquids encompassing pyridinium hydrazone-phenoxy conjugates as antimicrobial agents targeting diverse high resistant microbial strains

A focused library of new dicationic ionic liquids (DiILs) 6–41 appended pyridinium hydrazone and phenoxy side chain hybrids as counter cations were designed and synthesized, utilizing quaternization and metathesis reactions under both conventional and microwave irradiation. The novel DiILs 6–41 were fully characterized using different spectroscopic tools (1H, 13C, 19F, 11B, 31P NMR and mass spectra) and evaluated for their antimicrobial activity against diverse types of high resistant strains including two Gram-positive bacteria; methicillin-resistant Staphylococcus aureus (MRSA), Clostridium difficile, two Gram-negative bacteria; two Escherichia coli isolates, and Neisseria gonorrhea, and fungal strain; Candida albicans. The antibacterial screening was carried out by broth microdilution method and MIC values were reported as indicator of growth inhibition. They mostly exhibited antibacterial effect against MRSA and EC strains. The effect of the synthesized ILs on Gram-positive bacteria showed the phenoxy linker chain increases, the MIC values increases with more lethal effect due to the hydrophobicity parameter. This behavior was confirmed by the molecular dynamic simulation through the interaction with surface membrane as general mechanism of ILs. The dicationic ionic liquids are considered promising motifs for further investigations with focusing on the terminal hydrophobic adjuster.

Design, synthesis, in-silico and in-vitro evaluation of di-cationic pyridinium ionic liquids as potential anticancer scaffolds

An array of dicationic pyridinium ionic liquids (DILs) based hydrazone linkage were designed and synthesized via the quaternization of the appropriate bispyridine hydrazone with different phenacyl halides and led to the formation of halogenated DILs, which undergo metathesis reaction to give the specific task dicationic pyridinium liquids carrying fluorinated counter anions (PF6 ?, BF4 ?, CF3COO?). The newly synthesized DILs were well characterized using whole spectroscopic data. The Anticancer evaluation of DILs against breast and colon cancer cell lines revealed that compound 22 appears to be the most active compound in the series with IC50 in the two-digit micromolar range. The in-vitro anticancer results were further supported by in-silico molecular docking studies revealing the highest potency of compound 22. The docking analysis demonstrated good docking score and binding affinities of the synthesized compounds on the target protein PI3Kinase.

pH-Induced formation of metalloligand: Increasing structure dimensionality by tuning number of ligand functional sites

Two complexes, 2D [Cu2(CN)2(4-Hpcih)]n and 3D {[Cu2(CN)1.5(4-pcih)]·1.25H2O} n (4-Hpcih = 4-pyridinecarbaldehyde isonicotinoyl hydrazone), were obtained using a synthetic approach of pH-induced formation of metalloligands, successfully demonstrating a strategy to increase structure dimensionality by tuning the number of ligand functional sites. The Royal Society of Chemistry.

N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1

The expression of β-lactamases, especially metallo-β-lactamases (MβLs) in bacteria is one of the main causes of drug resistance. In this work, an effective N-acylhydrazone scaffold as MβL inhibitor was constructed and characterized. The biological activity assays indicated that the synthesized N-acylhydrazones 1–11 preferentially inhibited MβL NDM-1, and 1 was found to be the most effective inhibitor with an IC50 of 1.2 μM. Analysis of IC50 data revealed a structure–activity relationship, which is that the pyridine and hydroxylbenzene substituents at 2-position improved inhibition of the compounds on NDM-1. ITC and enzyme kinetics assays suggested that it reversibly and competitively inhibited NDM-1 (Ki = 0.29 ± 0.05 μM). The synthesized N-acylhydrazones showed synergistic antibacterial activities with meropenem, reduced 4–16-fold MIC of meropenem on NDM-1- producing E. coli BL21 (DE3), while 1 restored 4-fold activity of meropenem on K. pneumonia expressing NDM-1 (NDM-K. pneumoniae). The mice experiments suggested that 1 combined meropenem to fight against NDM-K. pneumoniae infection in the spleen and liver. Cytotoxicity assays showed that 1 and 2 have low cytotoxicity. This study offered a new framework for the development of NDM-1 inhibitors.

Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole

A new series of antinociceptive compounds belonging to the N- acylarylhydrazone (NAH) class were synthesized from natural safrole (7). The most analgesic derivative represented by 10f, [(4'-N,N- dimethylaminobenzylidene-3-(3',4'-methylenedioxyphenyl)propionylhydrazine], was more potent than dipyrone and indomethacin, used as standards. The NAH compounds described herein were structurally planned by molecular hybridization and classical bioisosterism strategies on previously reported analgesic NAH in order to identify the pharmacophoric contribution of the N- acylarylhydrazone moiety and investigate the structure-activity relationship (SAR) in these series. (C) 2000 Editions scientifiques et medicales Elsevier SAS.