19872-91-4

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl 4-hydroxypyridine-2,6-dicarboxylate is used as an intermediate in the synthesis of various drugs for its versatile chemical properties and potential therapeutic effects.
Used in Antioxidant and Anti-inflammatory Applications:
Dimethyl 4-hydroxypyridine-2,6-dicarboxylate is used as a potential antioxidant and anti-inflammatory agent, contributing to the development of new medications that target oxidative stress and inflammation-related conditions.
Used in Neurodegenerative Disease Treatment:
Dimethyl 4-hydroxypyridine-2,6-dicarboxylate is used as a potential therapeutic agent in the treatment of neurodegenerative diseases, leveraging its protective effects against cellular damage caused by oxidation.
Used in Cardiovascular Condition Management:
Dimethyl 4-hydroxypyridine-2,6-dicarboxylate is used in the management of cardiovascular conditions, potentially offering protective benefits against oxidative stress and inflammation in the cardiovascular system.
Used in Research and Development:
Dimethyl 4-hydroxypyridine-2,6-dicarboxylate is used in research and development for its ability to protect cells from damage caused by oxidation, aiding in the discovery of new therapeutic approaches and applications in medicine.

InChI:InChI=1S/C9H9NO5/c1-14-8(12)6-3-5(11)4-7(10-6)9(13)15-2/h3-4H,1-2H3,(H,10,11)

Upstream product

• 499-51-4 Chelidamic acid 
• 67-56-1 methanol 
• 138-60-3 chelidamic acid 
• 99-32-1 chelidonic acid 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 68854-18-2 2,4,6-trioxo-heptanedioic acid diethyl ester 
• 184870-12-0 chelidamic acid 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 99097-42-4 4-benzyloxypyridine-2,6-dicarboxylic dimethyl ester 
• 497103-48-7 4-[3,5-bis(benzyloxy)benzyloxy]pyridine-2,6-dicarboxylic acid dimethyl ester 
• 497103-51-2 4-[3,5-bis[3',5'-bis(benzyloxy)benzyloxy]benzyl]-pyridine-2,6-dicarboxylic dimethyl ester 
• 852201-11-7 4-[3,5-bis-(4-tert-butyl-benzyloxy)-benzyloxy]-pyridine-2,6-dicarboxylic acid dimethyl ester 
• 1309611-48-0 C₁₆H₁₆N₂O₅ 
• 1309611-49-1 C₂₈H₂₄N₆O₇ 
• 1364054-59-0 4-[(4-bromobenzyl)oxy]pyridine-2,6-dicarbaldehyde 
• 1364054-53-4 dimethyl 4-[(4-bromobenzyl)oxy]pyridine-2,6-dicarboxylate 
• 1450841-36-7 4-(3-((tert-butyldiphenylsilyl)oxy)propoxy)pyridine-2,6-dicarbaldehyde 
• 1450841-35-6 (4-(3-((tert-butyldiphenylsilyl)oxy)propoxy)pyridine-2,6-diyl)dimethanol 
• 1450841-34-5 dimethyl 4-(3-((tert-butyldiphenylsilyl)oxy)propoxy)pyridine-2,6-dicarboxylate 
• 680180-73-8 4-[3,5-bis-(3,5-bis-benzyloxy-benzyloxy)-benzyloxy]-pyridine-2,6-dicarboxylic acid 
• 497103-50-1 4-[3,5-bis(benzyloxy)benzyloxy]-pyridine-2,6-dicarboxylic acid 
• 944244-36-4 4-((E)-5-p-tolylpent-4-enyloxy)pyridine-2,6-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

The herringbone helix: A noncanonical folding in aromatic-aliphatic peptides

Hybrid oligomeric sequences derived from both aliphatic and aromatic units are shown to adopt a folded conformation with an unprecedented architecture. Specifically, a δ-amino acid bearing an aliphatic amine-6-aminomethyl-2-pyridinecarboxylic (P)-was designed and synthesized as a flexible analogue of 6-amino-2-quinolinecarboxylic acid (Q). Oligomers Pn (n = 2, 4, 8) were first synthesized but show no sign of folding in solution in organic solvents, unlike the Qn oligomers from which they are derived, which adopt particularly stable helical conformations. Hybrid oligomers (PQ)n (n = 1, 2, 4) were also prepared and were shown to adopt a novel folded conformation in the solid state where PQ units arrange into two stacks at a 90° angle from each other. Comprehensive NMR studies demonstrate that in solution this peculiar organization coexists with a helical conformation resembling that of Qn oligomers. Copyright

Poly(ethylene glycol)-supported chiral pyridine-2,6-bis(oxazoline): synthesis and application as a recyclable ligand in CuI-catalyzed enantioselective direct addition of terminal alkynes to imines

Pyridine-2,6-bis(oxazoline) immobilized on a soluble support, viz., poly(ethylene glycol) methyl ether with Mn = 5000 Da, has been synthesized for the first time. The efficiency of its application as a chiral ligand in CuI-catalyzed

Catenane-based mechanically-linked block copolymers

An original strategy for the synthesis of diblock copolymers where the blocks are linked by a catenane junction is described. Starting from a functionalized catenane precursor, our strategy enables the preparation of a variety of copolymers by different techniques such as ROP, ATRP and CuAAC click reaction.

Synthesis of 2,6-di(1,8-naphthyridin-2-yl)pyridines functionalized at the 4-position: Building blocks for suitable metal complex-based dyes

This study reports the synthesis of a methoxy-substituted 2,6-di(1,8-naphthyridin-2-yl)pyridine using Friedl?nder methodology. The functionalization at the 4-carbon of the methoxy-substituted derivative was confirmed by X-ray structural analysis. Finally, the methyl ether protecting group was cleaved to obtain 2,6-di(1,8-naphthyridin-2-yl)pyridine-4-ol. Using the compounds, coordination behavior to ruthenium(II) center was also examined.

Pyridine-based lanthanide complexes: Towards bimodal agents operating as near infrared luminescent and MRI reporters

We report two prototype Ln3+ complexes that address requirements for both MRI and luminescence imaging and we demonstrate that the presence of two H2O molecules bound to the Ln3+, beneficial for MRI applications of the Gd3+ analogue, is not a major limitation for the development of NIR luminescent agents. The Royal Society of Chemistry 2008.

New Proton-ionizable Macrocyclic Ligands. Synthesis, Basicity, Reactions, and Structures of Two Aza Crown Ethers containing the 4-Hydroxypyridine Unit

Two new reactive aza crown ethers, (1) and (2), containing the 4-hydroxypyridine unit have been prepared and found to be different with respect to pK(H2O) values for H2L(+), structures of the hydrates of HL, and complex formation with benzylamine and the benzylammonium ion.

Poly(ethylene glycol) modified Mn2+ complexes as contrast agents with a prolonged observation window in rat MRA

A novel rigid Mn2+ complex (MnL) with pyridine and pyrrolidine rings was designed and synthesized. The complex was further modified with alkyne, and conjugated to azide-terminated PEG by click chemistry. PEGylated MnL shows considerably higher relaxivity (MnL-PEG2k-MnL: r1 = 6.38 mmol-1 s-1; MnL-PEG4.6k-MnL: r1 = 5.63 mmol-1 s-1) and much longer blood circulation time than free Mn2+ complexes (MnL: r1 = 3.73 mmol-1 s-1), providing a prolonged time window to acquire longitudinal images for rat contrast enhanced magnetic resonance angiography.

Synthesis and evaluation of a rationally designed click-based library for G-Quadruplex selective DNA photocleavage

DNA containing repeating G-rich sequences can adopt higher-order structures known as G-quadruplexes (G4). These structures are believed to form within telomeres and the promoter regions of some genes, particularly in a number of proto-oncogenes, where they may play a role in regulating transcription. Alternatively, G4 DNA may act as a barrier to replication. To investigate these potential biological roles, probes that combine highly selective G4 DNA targeting with photocleavage activity can allow temporal detection of G4 DNA, providing opportunities to obtain novel insights about the biological roles of G4 DNA. We have designed, synthesized, and screened a small library of potential selective G-quadruplex DNA photocleavage agents incorporating the G-quadruplex targeting moiety of 360A with known photocleavage groups linked via "click" chemistry.

Surface engineering of silica nanoparticles with a gadolinium-PCTA complex for efficient: T1-weighted MRI contrast agents

New pyridine containing triAza; 3,6,9,15-tetraazabicyclo[9.3.1]pentadeca-1(15),11,13-triene-3,6,9-triacetic acid (PCTA) ligands presenting pendant carboxylic acid or alcohol functions have been synthesized and used to form diaqua Gd(iii) complexes, which

Spectroscopic and DFT Characterization of a Highly Reactive Nonheme FeV-Oxo Intermediate

The reaction of [(PyNMe3)FeII(CF3SO3)2], 1, with excess peracetic acid at -40 °C generates a highly reactive intermediate, 2b(PAA), that has the fastest rate to date for oxidizing cyclohexane by a nonheme iron species. It exhibits an intense 490 nm chromophore associated with an S = 1/2 EPR signal having g-values at 2.07, 2.01, and 1.94. This species was shown to be in a fast equilibrium with a second S = 1/2 species, 2a(PAA), assigned to a low-spin acylperoxoiron(III) center. Unfortunately, contaminants accompanying the 2(PAA) samples prevented determination of the iron oxidation state by M?ssbauer spectroscopy. Use of MeO-PyNMe3 (an electron-enriched version of PyNMe3) and cyclohexyl peroxycarboxylic acid as oxidant affords intermediate 3b(CPCA) with a M?ssbauer isomer shift δ = -0.08 mm/s that indicates an iron(V) oxidation state. Analysis of the M?ssbauer and EPR spectra, combined with DFT studies, demonstrates that the electronic ground state of 3b(CPCA) is best described as a quantum mechanical mixture of [(MeO-PyNMe3)FeV(O)(OC(O)R)]2+ (～75%) with some FeIV(O)(?OC(O)R) and FeIII(OOC(O)R) character. DFT studies of 3b(CPCA) reveal that the unbound oxygen of the carboxylate ligand, O2, is only 2.04 ? away from the oxo group, O1, corresponding to a Wiberg bond order for the O1-O2 bond of 0.35. This unusual geometry facilitates reversible O1-O2 bond formation and cleavage and accounts for the high reactivity of the intermediate when compared to the rates of hydrogen atom transfer and oxygen atom transfer reactions of FeIII(OC(O)R) ferric acyl peroxides and FeIV(O) complexes. The interaction of O2 with O1 leads to a significant downshift of the Fe-O1 Raman frequency (815 cm-1) relative to the 903 cm-1 value predicted for the hypothetical [(MeO-PyNMe3)FeV(O)(NCMe)]3+ complex.