698973-85-2

Usage

Type of compound

Organic, heterocyclic

Classification

Naphthyridine class of chemicals

Physical appearance

Yellow crystalline solid

Primary use

Intermediate in the synthesis of pharmaceuticals

Structural features

Naphthyridine ring, two methyl groups, one carbonyl group

Industrial applications

Pharmaceutical and chemical industries

Unique attributes

Structure and reactivity

Upstream product

• 698973-81-8 3-(4,6-dimethyl-2-ylamino)propanoic acid 
• 5407-87-4 2-Amino-4,6-dimethylpyridine 

Downstream Products

• 65541-95-9 5,7-dimethyl-1,2,3,4-tetrahydro[1,8]naphthyridine 
• 698974-42-4 6-bromo-5,7-dimethyl-1,2,3,4-tetrahydro[1,8]naphthyridine 

Relevant academic research and scientific papers

PYRAZOLE COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES

The present invention relates to pharmaceutical compositions comprising compounds of the Formula (I), and methods of selectively inhibiting or antagonizing the αVβ3 and/or the α Vβ5 integrin without significantly inhibitin

Synthesis and reactivity of some 6-substituted-2,4-dimethyl-3-pyridinols, a novel class of chain-breaking antioxidants

The synthesis and study of a series of 6-substituted-2,4-dimethyl-3- pyridinols having interesting antioxidant properties is reported. The general synthetic strategy leading to the compounds involved a low-temperature aryl bromide-to-alcohol conversion as the last step. 2,4-Dimethyl-3-pyridinol (1a), 2,4,6-trimethyl-3-pyridinol (1b), and 2,4-dimethyl-6-(dimethylamino)-3-pyridinol (1d) were thus prepared from the corresponding 3-bromopyridine precursor. The methoxy derivative 2,4-dimethyl-6-(methoxy)-3-pyridinol (1c) was also prepared by an alternate route via a Baeyer-Villiger reaction on the substituted benzaldehyde precursor. Novel bicyclic pyridinols 2 and 3 required prior construction of the ring structure. Thus, 2 was prepared by the use of a 6-step intramolecular Friedel-Crafts strategy, and 3 required an 11-step sequence with a thermolytic intramolecular inverse-demand Diels-Alder reaction between a pyrimidine ring and an alkyne as the key step. Basicities of the pyridinols approached physiological pH with increasing electron density in the ring. Pyridinols 1a-d were found to be indefinitely stable to air oxidation while 2 and 3 decomposed upon extended exposure to the atmosphere. The reactivities of the pyridinols toward chain-carrying peroxyl radicals in homogeneous organic solution were examined by studying the kinetics of radical-initiated styrene autoxidations under controlled conditions. These experiments revealed that some of the newly synthesized pyridinols are the most effective phenolic chain-breaking antioxidants reported to date.