4808-64-4

Usage

Uses

Used in Chemical and Biological Research:
2,6-DIMETHYL-4-NITROPYRIDINE-1-OXIDE is used as a stable free radical in various research applications, particularly for its ability to participate in reactions without being consumed, which is valuable for studying reaction mechanisms and kinetics.
Used in Electron Paramagnetic Resonance (EPR) Spectroscopy:
2,6-DIMETHYL-4-NITROPYRIDINE-1-OXIDE is utilized as a spin label in EPR spectroscopy studies. It aids in probing the local environment and dynamics of molecules, offering insights into molecular structure and interactions.
Used as a Photoinitiator in Polymerization Processes:
In the field of materials science, 2,6-DIMETHYL-4-NITROPYRIDINE-1-OXIDE serves as a photoinitiator, triggering the polymerization of monomers upon exposure to light. This application is crucial for the development of new polymer materials with specific properties.
Used in Pharmaceutical Development:
2,6-DIMETHYL-4-NITROPYRIDINE-1-OXIDE has been investigated for its potential use in pharmaceuticals, where its unique properties may contribute to the development of new drugs or drug delivery systems.
Used as a Reagent in Organic Synthesis:
2,6-DIMETHYL-4-NITROPYRIDINE-1-OXIDE also finds application as a reagent in organic synthesis, where it can be used to modify or create new organic compounds, contributing to the advancement of organic chemistry.

InChI:InChI=1/C7H9N2O3/c1-5-3-7(9(11)12)4-6(2)8(5)10/h3-5H,1-2H3/q+1

Upstream product

• 1073-23-0 2,6-lutidine N-oxide 
• 1122-61-8 4-nitropyridine 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 108-48-5 2,6-dimethylpyridine 
• 54754-76-6 3-iodo-2,6-dimethyl-4-nitropyridine N-oxide 
• 6890-58-0 2,6-dimethylpyridine N-oxide hydrochloride 

Downstream Products

• 3512-75-2 4-chloro-2,6-lutidine 
• 90000-67-2 2,6-dimethyl-4-mercaptopyridine 
• 1250445-93-2 4-nitro-2,6-diacetylpyridine bis(2,4,6-trimethylphenylimine) 
• 4913-57-9 4-nitro-2,6-dimethylpyridine 
• 52062-26-7 4-methoxy-pyridine-2,6-dicarboxylic acid 
• 63897-10-9 4-nitro-pyridine-2,6-dicarboxylic acid 
• 5093-68-5 4-bromo-2,6-dimethyl-1-oxido-pyridin-1-ium 
• 358621-46-2 2,6-bis(bromomethyl)-4-nitropyridine 
• 20815-02-5 4-methoxy-2,6-dimethylpyridine 
• 98278-85-4 4-chloro-3,5-diiodo-pyridine-2,6-dicarboxylic acid 
• 98273-74-6 4-chloro-3,5-diiodo-2,6-dimethyl-pyridine 
• 142590-65-6 Acetic acid 4-ethoxy-6-methyl-pyridin-2-ylmethyl ester 
• 193690-74-3 3,4,6-Trimethyl-3H-imidazo[4,5-c]pyridin-2-ylamine 
• 193690-78-7 3-amino-2,6-dimethyl-4-(methylamino)pyridine 

Relevant academic research and scientific papers

TGF-beta receptor inhibitor

The invention provides a compound shown as a formula (I) and a pharmaceutical composition thereof. The compound shown as the formula (I) of the present invention is useful as a TGF-beta receptor inhibitor, particularly a TGF beta RI inhibitor, for example, in the prevention or treatment of various TGF beta RI (ALK5) mediated related diseases.

Electronic influence of substitution on the pyridine ring within NNN pincer-type molecules

Pincer molecules are of increasing interest due to the modular nature of modification and range of reactivity observed when coordinated to metal ions. A subset within the family of pincer molecules use a pyridine group to bridge the outer two arms as well as provide a N-donor atom for metal binding. While the arm appendages have been studied extensively, little research has been conducted on the electronic effects of the central, substituted pyridine systems. Therefore, a series of NNN pincer-type ligands with substitution on the 4-position of the pyridine ring with -OH, -OBn, -H, -Cl, and -NO2 functional groups were synthesized and characterized through NMR spectroscopy and ESI-HRMS. Each pincer was metalated with Cu(ii) salts and evaluated through X-ray diffraction analysis, cyclic voltammetry, and density functional theory analysis. The results indicate that the relatively unstudied -OBn group demonstrates both electron-withdrawing (XRD bond lengths) and electron-donating (NMR spectroscopy) properties. The -NO2 pincer ligand shows a redox event within experimental windows evaluated, in contrast to the other congeners studied. In addition, electron-donating groups increase the electron density around the Cu(ii) center based on DFT studies and cyclic voltammetry. These findings can be applied to other pyridine-based pincer systems when considering ligand design and warrants future characterization of 4-position substituted pyridines.

Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups

The number of substituted pyridine pyridinophanes found in the literature is limited due to challenges associated with 12-membered macrocycle and modified pyridine synthesis. Most notably, the electrophilic character at the 4-position of pyridine in pyridinophanes presents a unique challenge for introducing electrophilic chemical groups. Likewise, of the few reported, most substituted pyridine pyridinophanes in the literature are limited to electron-donating functionalities. Herein, new synthetic strategies for four new macrocycles bearing the electron-withdrawing groups CN, Cl, NO2, and CF3 are introduced. Potentiometric titrations were used to determine the protonation constants of the new pyridinophanes. Further, the influence of such modifications on the chemical behavior is predicted by comparing the potentiometric results to previously reported systems. X-ray diffraction analysis of the 4-Cl substituted species and its Cu(II) complex are also described to demonstrate the metal binding nature of these ligands. DFT analysis is used to support the experimental findings through energy calculations and ESP maps. These new molecules serve as a foundation to access a range of new pyridinophane small molecules and applications in future work.

Stable and rigid DTPA-like paramagnetic tags suitable for in vitro and in situ protein NMR analysis

Organic synthesis of a ligand with high binding affinities for paramagnetic lanthanide ions is an effective way of generating paramagnetic effects on proteins. These paramagnetic effects manifested in high-resolution NMR spectroscopy are valuable dynamic and structural restraints of proteins and protein–ligand complexes. A paramagnetic tag generally contains a metal chelating moiety and a reactive group for protein modification. Herein we report two new DTPA-like tags, 4PS-PyDTTA and 4PS-6M-PyDTTA that can be site-specifically attached to a protein with a stable thioether bond. Both protein-tag adducts form stable lanthanide complexes, of which the binding affinities and paramagnetic tensors are tunable with respect to the 6-methyl group in pyridine. Paramagnetic relaxation enhancement (PRE) effects of Gd(III) complex on protein-tag adducts were evaluated in comparison with pseudocontact shift (PCS), and the results indicated that both 4PS-PyDTTA and 4PS-6M-PyDTTA tags are rigid and present high-quality PREs that are crucially important in elucidation of the dynamics and interactions of proteins and protein-ligand complexes. We also show that these two tags are suitable for in-situ protein NMR analysis.

Preparation and purification method of toxic impurity DCAL of clopidol

The invention relates to a preparation and purification method of toxic impurity DCAL of clopidol and belongs to the technical field of preparation of standard medicine products. The preparation and purification method comprises the following steps: firstly carrying out chlorination reaction, i.e., dissolving a solvent and 2,6-dimethyl-4-aminopyridine; then slowly adding a chlorinating agent to carry out chlorination; after reaction is finished, carrying out neutralization and water washing, concentration and crystallization, filtering or direct neutralization and filtering on reaction liquidto obtain a crude DCAL product; purifying the crude DCAL product, adding a mixed solvent of ethanol and ethyl acetate into the crude DCAL product, stirring for dissolving, dripping petroleum ether toprecipitate solids, filtering, carrying out concentration, cooling and precipitation on filtrate, then filtering, and drying solids to obtain a pure DCAL product. The preparation and purification method has the beneficial effects that the reaction temperature is low, the reaction time is short, the side products in reaction are fewer, and the product is easily purified, so that convenience is brought for preparing impurity reference products of the veterinary-drug clopidol.

Generic tags for Mn(II) and Gd(III) spin labels for distance measurements in proteins

High-affinity chelating tags for Gd(iii) and Mn(ii) ions that provide valuable high-resolution distance restraints for biomolecules were used as spin labels for double electron-electron resonance (DEER) measurements. The availability of a generic tag that can bind both metal ions and provide a narrow and predictable distance distribution for both ions is attractive owing to their different EPR-related characteristics. Herein we introduced two paramagnetic tags, 4PSPyMTA and 4PSPyNPDA, which are conjugated to cysteine residues through a stable thioether bond, forming a short and, depending on the metal ion coordination mode, a rigid tether with the protein. These tags exhibit high affinity for both Mn(ii) and Gd(iii) ions. The DEER performance of the 4PSPyMTA and 4PSPyNPDA tags, in complex with Gd(iii) or Mn(ii), was evaluated for three double cysteine mutants of ubiquitin, and the Gd(iii)-Gd(iii) and Mn(ii)-Mn(ii) distance distributions they generated were compared. All three Gd(iii) complexes of the ubiquitin-PyMTA and ubiquitin-PyNPDA conjugates produced similar and expected distance distributions. In contrast, significant variations in the maxima and widths of the distance distributions were observed for the Mn(ii) analogs. Furthermore, whereas PyNPDA-Gd(iii) and PyNPDA-Mn(ii) delivered similar distance distributions, appreciable differences were observed for two mutants with PyMTA, with the Mn(ii) analog exhibiting a broader distance distribution and shorter distances. ELDOR (electron-electron double resonance)-detected NMR measurements revealed some distribution in the Mn(ii) coordination environment for the protein conjugates of both tags but not for the free tags. The broader distance distributions generated by 4PSPyMTA-Mn(ii), as compared with Gd(iii), were attributed to the distributed location of the Mn(ii) ion within the PyMTA chelate owing to its smaller size and lower coordination number that leave the pyridine nitrogen uncoordinated. Accordingly, in terms of distance resolution, 4PSPyNPDA can serve as an effective generic tag for Gd(iii) and Mn(ii), whereas 4PSPyMTA is efficient for Gd(iii) only. This comparison between Gd(iii) and Mn(ii) suggests that PyMTA model compounds may not predict sufficiently well the performance of PyMTA-Mn(ii) as a tag for high-resolution distance measurements in proteins because the protein environment can influence its coordination mode.

Single-armed phenylsulfonated pyridine derivative of DOTA is rigid and stable paramagnetic tag in protein analysis

Single-armed DOTA-like phenylsulfonated pyridine derivatives are rigid and stable paramagnetic tags for site-specific labeling of proteins. Their reactions with a solvent-exposed protein thiol group generate a stable C-S bond and produce one single paramagnetic species in solution NMR. The generated large paramagnetic effects yield valuable long-range structural restraints for proteins.

DTTA paramagnetic probe for protein labeling

The invention discloses a DTTA paramagnetic probe for protein paramagnetic labeling. The chemical name of the paramagnetic probe is 4-phenylsulfonyl-6-methyl-2-[N, N-bis(ethylenediamine)aminomethyl]pyridine-N', N', N'', N''-tetraacetic acid, and the chemical structural formula is shown as the specification. The probe has eight coordination sites, contains four carboxyl groups, three nitrogen atoms and one pyridine nitrogen, and achieves rigid connection by means of nucleophilic substitution reaction between para-position phenylsulfonyl of pyridine ring and protein sulfhydryl in an aqueous solution. The DTTA paramagnetic probe for protein paramagnetic labeling provided by the invention can be directly used for protein labeling. The probe provided by the invention has eight coordination sites, contains four carboxyl groups, three nitrogen atoms and one pyridine nitrogen, achieves rigid connection through reaction of phenylsulfonyl and protein sulfhydryl, has the advantages of high denticity, good chelating properties (a plurality of coordination sites), single conformation, and good water solubility, and can be directly used for protein labeling.

Metal-free methylation of a pyridine N-oxide C-H bond by using peroxides

Metal-free methylation of a pyridine N-oxide C-H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO2, and OCH3) were all suitable substrates, and the desired products were obtained in moderate to excellent yields under standard conditions. Moreover, the methylation can be performed with a good yield on the gram-scale experiment. Tentative mechanistic studies show that the methylation is a classical radical process.

Kinetic assay of the michael addition-like thiol-ene reaction and insight into protein bioconjugation

The chemical modification of proteins is a valuable technique in understanding the functions, interactions, and dynamics of proteins. Reactivity and selectivity are key issues in current chemical modification of proteins. The Michael addition-like thiol-ene reaction is a useful tool that can be used to tag proteins with high selectivity for the solvent-exposed thiol groups of proteins. To obtain insight into the bioconjugation of proteins with this method, a kinetic analysis was performed. New vinyl-substituted pyridine derivatives were designed and synthesized. The reactivity of these vinyl tags with L-cysteine was evaluated by UV absorption and high-resolution NMR spectroscopy. The results show that protonation of pyridine plays a key role in the overall reaction rates. The kinetic parameters were assessed in protein modification. The different reactivities of these vinyl tags with solvent-exposed cysteine is valuable information in the selective labeling of proteins with multiple functional groups. Tag! You're it! The Michael addition-like thiol-ene reaction between a pyridine-substituted vinyl group and the thiol of L-cysteine is evaluated by kinetic assay. Diverse reaction rates between different vinyl tags and free thiols are assessed, and the determined reactivity offers valuable information on protein bioconjugation.