1849-49-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-2,5-dimethylpyridine-4-carboxaldehyde is used as an intermediate in the synthesis of various drugs, including antimalarial and antitumor agents, due to its potential to interact with biological receptors and enzymes.
Used in Drug Discovery and Development:
3-Hydroxy-2,5-dimethylpyridine-4-carboxaldehyde is utilized as a key component in the development of new drugs, leveraging its ability to bind with biological targets and modulate their activity, which can lead to the discovery of novel therapeutic agents.
Used in Manufacturing of Dyes and Pigments:
3-Hydroxy-2,5-dimethylpyridine-4-carboxaldehyde is employed as a chemical intermediate in the production of dyes and pigments, contributing to the coloration and stability of these products.
Used in Synthesis of Specialized Chemicals:
3-HYDROXY-2,5-DIMETHYLPYRIDINE-4-CARBOXALDEHYDE is also used in the synthesis of other specialized chemicals, where its unique structural features and functional groups can be exploited to create compounds with specific properties and applications.

InChI:InChI=1/C8H9NO2/c1-5-3-9-6(2)8(11)7(5)4-10/h3-4,11H,1-2H3

Upstream product

• 4811-03-4 5'-Deoxypyridoxine 
• 220092-30-8 <5-hydroxy-4-(hydroxymethyl)-6-methylpyridin-3-yl>methyl acetate 
• 58-56-0 pyridoxal hydrochloride 
• 6562-92-1 chlorhydrate de la 5-(chloromethyl)-2,2,8-trimethyl-4H-1,3-dioxino<4,5-c>pyridine 
• 6953-28-2 (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol hydrochloride 
• 911142-35-3 2-amino-3-(carboxymethyl-amino)-3-(3-hydroxy-2,5-dimethyl-pyridin-4-yl)-propionic acid 
• 143571-93-1 4-[(E)-Hexyliminomethyl]-2,5-dimethyl-pyridin-3-ol 
• 128669-12-5 4-[(E)-Hexyliminomethyl]-2,5-dimethyl-pyridin-3-ol 
• 65-22-5 pyridoxal hydrochloride 
• 78313-60-7 2-Methyl-3-hydroxy-4-methoxymethyl-5-chloromethylpyridine hydrochloride 

Downstream Products

• 132120-30-0 2,5-Dimethyl-4-phenylaminomethyl-pyridin-3-ol 
• 132120-36-6 5,8-Dimethyl-3-phenyl-3,4-dihydro-2H-pyrido[4,3-e][1,3]oxazine 

Relevant academic research and scientific papers

INHIBITORS OF THE KYNURENINE PATHWAY

The present application provides novel inhibitors of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase, metabolites thereof, and phannaceutically acceptable salts or prodrugs thereof. Also provided are methods for preparing these compounds. A therapeutically effective amount of one or more of the compounds of formula (I) is useful in treating diseases resulting from dysregulation of the kynurenine pathway. Compounds of formula (I) act by inhibiting the enzymatic activity or expression of indoleamine 2,3-dioxygenase-1 and/or indoleamine 2,3-dioxygenase-2 and/or tryptophan 2,3-dioxygenase.

Claisen-type addition of glycine to a pyridoxal iminium ion in water

The 5′-deoxypyridoxal stabilized glycine carbanion has been generated in water at neutral and mildly basic pH. At pH 7, this carbanion reacts mainly with the carbonyl carbon of 1 to form a stable Claisen-type adduct. At pH ≥ 8, this carbanion reacts with the iminium carbon of the pyridoxalglycine iminium ion to form the second Claisen-type adduct 3 as the major reaction product.

Band-shape Analysis of Electronic Spectra and Study of the Hydrolysis of the Schiff Bases of 5'-Deoxypyridoxal and n-Hexylamine in Aqueous and Non-aqueous Media

The bands of the absorption spectra of the Schiff bases formed between 5'-deoxypyridoxal (DPL) and n-hexylamine in various aqueous solvents (water-dioxane mixtures) and non-aqueous media (dioxane, pentanol-dioxane mixtures, pentanol, butan-2-ol, propanol, ethanol and methanol) have been analysed at 25 deg C.We have also calculated the hydrolysis rate constants of the different tautomers of the Schiff bases.According to our results, the zwitterionic and enol tautomers are more stable on account of the formation of very stable hydrogen bonds.On the other hand, theion-dipole form is the most reactive owing to the absence of stabilizing intramolecular hydrogen bonds and the protonated state of its pyridine nitrogen.The results obtained in this work also show that the relative permittivity of the medium does not significantly affect the tautomeric equilibrium of the chemical species of the Schiff bases of DPL and n-hexylamine.Marshall plots reveal that the microscopic pK most markedly influenced by solvation is that of the phenolic oxygen, whereas that of the pyridine nitrogen is absolutely insensitive to solvation.

Formation of Schiff Bases of 5'-Deoxypyridoxal and Hexylamine in Aqueous and Non-aqueous Media

We have studied the formation of Schiff bases of 5'-deoxypyridoxal (DPL) and hexylamine in various non-aqueous solvents (dioxane, pentanol/dioxane mixtures, pentanol, butan-2-ol, propanol, ethanol, methanol and ethane-1,2-diol) at 25 deg C.The results are interpreted in terms of the tautomer forms of DPL present in the medium, and the rate constant of formation of the Schiff base has been obtained for the neutral species of DPL and the zwitterionic form (k1n = 1.7 * 102 dm3 mol-1 min-1 and k2z = 3.6 * 103 dm3 mol-1 min-1, respectively).We also determined the constant of the tautomeric equilibrium between the corresponding forms of the uncharged species of DPL in the different solvents.These results and those obtained in water/dioxane media indicate that the intramolecular acid catalysis involved in the formation of Schiff bases is also governed by the occurrence of a charged transition state.