5112-36-7

Basic information

• Product Name: Pyridine-2,6-dicarbohydrazide
• Synonyms: PYRIDINE 2,6-DICARBOXYLIC DIHYDRAZIDE;Pyridine-2,6-dicarbohydrazide
• CAS NO: 5112-36-7
• Molecular Formula: C₇H₉N₅O₂
• Molecular Weight: 195.18
• EINECS: 203-963-7
• Mol File: 5112-36-7.mol
• Article Data: 31

Chemical Properties

• Appearance: /
• Density: 1.417g/cm³
• Refractive Index: 1.636
• CAS DataBase Reference: Pyridine-2,6-dicarbohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine-2,6-dicarbohydrazide(5112-36-7)
• EPA Substance Registry System: Pyridine-2,6-dicarbohydrazide(5112-36-7)

Safety Data

• Hazardous Substances Data: 5112-36-7(Hazardous Substances Data)

Usage

General Description

Pyridine-2,6-dicarbohydrazide, also known as 2,6-Pyridinedicarbohydrazide or di(isonicotinic acid) hydrazide, is a chemical compound that contains a pyridine ring and two carbohydrazide groups. It is commonly used as a precursor in the synthesis of pharmaceuticals, agrochemicals, and dyes. Pyridine-2,6-dicarbohydrazide is known for its high melting point and is insoluble in water, but soluble in organic solvents. Its unique structure and chemical properties make it a valuable intermediate for various chemical reactions and applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C7H9N5O2/c8-11-6(13)4-2-1-3-5(10-4)7(14)12-9/h1-3H,8-9H2,(H,11,13)(H,12,14)

Upstream product

• 15658-60-3 diethyl-2,6-pyridinedicarbonyl ester 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 1129-30-2 2,6-Diacetylpyridine 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 

Downstream Products

• 28356-35-6 N'2,N'6-di((E)-benzylidene)pyridine-2,6-dicarbohydrazide 
• 1020170-54-0 pyridine-2,6-dicarboxylic acid bis-(N'-benzenesulfonyl-hydrazide) 
• 75559-47-6 ZrO(C₆H₅CNNCOC₅H₃NCONNCCH₂CH₃)(H₂O)2 
• 1100081-88-6 N₂',N₆'-bis(4-chlorobenzoyl)pyridine-2,6-dicarbohydrazide 
• 376624-79-2 N'2,N'6-bis(4-methoxybenzylidene)pyridine-2,6-dicarbohydrazide 
• 507445-69-4 N'2,N'6-bis(4-chlorobenzylidene)pyridine-2,6-dicarbohydrazide 
• 25433-35-6 2,6-bis(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine 
• 1338709-66-2 2,6-bis(4-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyridine 
• 1338709-65-1 N'2,N'6-bis(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl)pyridine-2,6-dicarboxamide 
• 1338709-64-0 2,6-bis[5-(4-chorophenyl)-1,3,4-thiadiazol-2-yl]pyridine 
• 1338709-63-9 2,6-bis[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-y1]pyridine 
• 872200-46-9 2,6-bis[4-nitrophenyl(thioureidocarbomoyl)]pyridine 
• 75559-48-7 ZrO(C₆H₅CNNCOC₅H₃NCONNCCH₂C₆H₅)(H₂O)2 
• 90017-09-7 2,6-Bis-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine 

Relevant articles and documents

2,6-Pyridinedicarbohydrazide-Salicylal hydrazone-base derivative with High detection limit and binding Constant for emissive ion chemosensing in aqueous solution

A new tridentate luminescent molecule, N2,N6-bis(salicylidene)pyridine-2,6-dicarbohydrazide (BSPDH), was introduced and facilely eco-synthesized with high yield. It was then characterized through Fourier transform infrared, Hydrogen-

Synthesis and characterization of bis[N′-(4-carboxybenzylidene)]- pyridine-2,6-dicarbohydrazide: Colorimetric and fluorometric modulation in presence of F- ions

(Graph Presented) A novel organic compound bis[N′-(4- carboxybenzylidene)]-pyridine-2,6-dicarbohydrazide (L) was synthesized and characterized using spectroscopic and X-ray diffraction techniques. Tetrabutyl ammonium halides [(Bu)4N+X-] X = F, Cl, Br and I were allowed to react separately with a solution of L in DMSO (1 × 10-5 M). The solution of L turned to shining yellow colour in the presence of F- ion only. The binding properties have been studied using absorption, emission and 1H NMR titrations. Theoretical studies on compound L and compound L + X- (X = F, Cl and Br) in DMSO medium were carried out using density functional theory (DFT) at the B3LYP/6-31G(d,p)/6-31G+(d,p) level. The theoretical calculations agreed to the experimental results.

2,6-Bis[(2-hydr-oxy-3-methoxy-benzyl-idene)hydrazinocarbon-yl]pyridine monohydrate

In the title compound, C23H19N5O6·H2O, the two components are linked into complex chains by a combination of two independent O - H...O and two independent N - H...O hydrogen bonds. The complex chains are linked into a two-dimensional sheet network via π-π

Dicarbohydrazide based chemosensors for copper and cyanide ions: Via a displacement approach

Ligands attached to pyridine dicarbohydrazide were synthesized and characterized by NMR, FT-IR, elemental analysis, UV-visible spectroscopy, mass spectrophotometry, emission spectra and single crystal X-ray diffraction. These ligands were found to recognize copper ions over other metal ions and cyanide ions by a copper complex performing an in situ experiment with turn on-off-on behaviour over different anions in a CH3OH:H2O (9:1, v/v solution) medium. These ligands displayed a red shift in their absorption spectra and quenching in their emission spectra when exposed to copper ions via a PET mechanism and a further copper complex was applied for cyanide detection among the other anions. The 1:2, 1:3, 1:2 and 1:2 stoichiometric ratios of the ligands (L1-L4, respectively) with copper ions were calculated from a Job plot based on the UV-visible spectra. The S-V plot represents the linearity of the ligands with copper ions. The limits of detection (LOD) of copper ions along with the ligands (L1-L4) were calculated to be 0.12, 0.10, 0.097 and 0.098 μM using emission spectra, respectively. The binding affinities of the ligands with copper ions were determined by various characterization techniques such as FTIR, mass spectrophotometry and electrochemical and optical studies. Furthermore, an in situ experiment was performed for cyanide detection via a metal displacement approach. L1 and L4 with Cu2+ ions showed an affinity towards cyanide ions, with detection limits of 0.31 and 0.53 μM.

Hydrazones in anion transporters: The detrimental effect of a second binding site

Synthetic anion transporters can be developed using anion receptors that are able to bind the anion and stabilize it in the lipophilic interior of a bilayer membrane, and they usually contain functional groups with acidic NHs, such as ureas, thioureas and squaramides. To assess the suitability of acylhydrazones as a new functional group for the preparation of anion transporters, we have studied a family of thioureas functionalized with these and related functional groups.1H NMR titrations and DFT calculations indicate that the thioureas bearing acylhydrazone groups behave as chloride receptors with two separate binding sites, of which the acylhydrazone binds weaker than the thiourea. Chloride transport studies show that the additional binding site has a detrimental effect on thiourea-based transporters, and this phenomenon is also observed for bis(thio)ureas with two separate binding sites. We propose that the presence of a second anion binding unit hinders the transport activity of the thiourea due to additional interactions with the phospholipids of the membrane. In agreement with this hypothesis, extensive molecular dynamics simulations suggest that the molecules will tend to be positioned in the water/lipid interface, driven by the interaction of the NHs of the thiourea and of the acylhydrazone groups with the POPC polar head groups and water molecules. Moreover, the interaction energies show that the poorest transporters have indeed the strongest interactions with the membrane phospholipids, inhibiting chloride transport. This detrimental effect of additional functional groups on transport activity should be considered when designing new ion transporters, unless these groups cooperatively promote anion recognition and transmembrane transport.

Novel cationic bis(acylhydrazones) as modulators of Epstein–Barr virus immune evasion acting through disruption of interaction between nucleolin and G-quadruplexes of EBNA1 mRNA

The oncogenic Epstein–Barr virus (EBV)evades the immune system through limiting the expression of its highly antigenic and essential genome maintenance protein, EBNA1, to the minimal level to ensure viral genome replication, thereby also minimizing the production of EBNA1-derived antigenic peptides. This regulation is based on inhibition of translation of the virally-encoded EBNA1 mRNA, and involves the interaction of host protein nucleolin (NCL)with G-quadruplex (G4)structures that form in the glycine–alanine repeat (GAr)-encoding sequence of the EBNA1 mRNA. Ligands that bind to these G4-RNA can prevent their interaction with NCL, leading to disinhibition of EBNA1 expression and antigen presentation, thereby interfering with the immune evasion of EBNA1 and therefore of EBV (M.J. Lista et al., Nature Commun., 2017, 8, 16043). In this work, we synthesized and studied a series of 20 cationic bis(acylhydrazone)derivatives designed as G4 ligands. The in vitro evaluation showed that most derivatives based on central pyridine (Py), naphthyridine (Naph)or phenanthroline (Phen)units were efficient G4 binders, in contrast to their pyrimidine (Pym)counterparts, which were poor G4 binders due to a significantly different molecular geometry. The influence of lateral heterocyclic units (N-substituted pyridinium or quinolinium residues)on G4-binding properties was also investigated. Two novel compounds, namely PyDH2 and PhenDH2, used at a 5 μM concentration, were able to significantly enhance EBNA1 expression in H1299 cells in a GAr-dependent manner, while being significantly less toxic than the prototype drug PhenDC3 (GI50 > 50 μM). Antigen presentation, RNA pull-down and proximity ligation assays confirmed that the effect of both drugs was related to the disruption of NCL–EBNA1 mRNA interaction and the subsequent promotion of GAr-restricted antigen presentation. Our work provides a novel modular scaffold for the development of G-quadruplex-targeting drugs acting through interference with G4–protein interaction.