161871-65-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-NITRO-4-PYRIDINYL)-ETHANONE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of nitro-substituted heterocyclic compounds, which are integral in medicinal chemistry for their potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(3-NITRO-4-PYRIDINYL)-ETHANONE is utilized as an intermediate in the production of agrochemicals, playing a role in the synthesis of compounds that can be used in pest control and crop protection due to their bioactive properties.
Used in Organic Synthesis:
1-(3-NITRO-4-PYRIDINYL)-ETHANONE is employed as a chiral auxiliary in asymmetric synthesis, a technique that is vital for the production of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical applications to ensure desired biological activity and minimize side effects.

InChI:InChI=1/C7H6N2O3/c1-5(10)6-2-3-8-4-7(6)9(11)12/h2-4H,1H3

Upstream product

• 1122-54-9 methyl (4-pyridyl) ketone 
• 161871-64-3 (R,S)-3-nitro-4-(1-hydroxyethyl)pyridine 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 13091-23-1 4-chloro-3-nitropyridine 

Downstream Products

• 16287-97-1 4-chloro-[1,7]naphthyridine 
• 60122-51-2 1,7-naphthyridin-4(1H)-one 
• 13210-52-1 1-(3-aminopyridin-4-yl)ethan-1-one 

Relevant academic research and scientific papers

A new efficient synthesis of 3-nitropyridine and substituted derivatives

Pyridine and pyridine derivatives have been nitrated in the β-position by reaction with N2O5 or NO2·BF4 in MeNO2, THF or MeCN to form the N-nitropyridinium salt. This was then reacted with an aqueous solution of a nucleophile to give the β-nitro compound in moderate to good yield.

ARYL LINKED IMIDAZOLE AND TRIAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR IMPROVING THE PHARMACOKINETICS OF A DRUG

The present invention relates to aryl linked imidazole and triazole derivatives, compositions comprising said compounds, alone or in combination with other drugs, and methods of using the compounds for improving the pharmacokinetics of a drug. The compounds of the invention are useful in human and veterinary medicine for inhbiting CYP3A4 and for improving the pharmacokinetics of a therapeutic compound that is metabolized by CYP3A4.

ARYL LINKED IMIDAZOLE AND TRIAZOLE DERIVATIVES AND METHODS OF USE THEREOF FOR IMPROVING THE PHARMACOKINETICS OF A DRUG

The present invention relates to aryl linked imidazole and triazole derivatives, compositions comprising said compounds, alone or in combination with other drugs, and methods of using the compounds for improving the pharmacokinetics of a drug. The compounds of the invention are useful in human and veterinary medicine for inhbiting CYP3A4 and for improving the pharmacokinetics of a therapeutic compound that is metabolized by CYP3A4.

Synthesis of novel 1,7-naphthyridines by Friedlaender condensation of pyridine substrates

The general ability of appropriate pyridyl compounds (aldehyde or ketone) to undergo Friedlaender condensation to give different 1,7-naphthyridines has been demonstrated. 2,4-Disubstituted 1,7-naphthyridine 8 was prepared from 3-amino-4-acetylpyridine (6) and ketone 4 (82%). The Friedlaender self-condensation of pyridyl substrate 6 is reported, as well. The dimer product, 2-(3-aminopyridin-4-yl)-4-methyl-1,7-naphthyridine (7), was obtained in 97% yield. 2-Aryl-and 2,3-diaryl-1,7-naphthyridines (16-18) were prepared from 3-aminoisonicotinaldehyde (13) and arylketones 4, 14, and 15 (28-71%). The key substrates 6 and 13 are readily available via the improved pyridine nitration method. Copyright

7-Azacinnolin-4(1H)-one preparation and NMR studies of tautomery

As part of our current investigations of nitropyridines, we hereby report the preparation of a new annulated heterocycle by C-azo coupling. Thus, the azacinnoline, pyrido[3,4-c]pyridazin-4(1H)-one (38%), was prepared from 4-acetyl-3-aminopyridine via diazotization. 1H, 13C, and 15N NMR spectroscopic investigations revealed that the azacinnoline exclusively exists in the NH-keto tautomeric form in DMSO-d6, CD 3OD, and D2O.

4-Pyridylanilinothiazoles that selectively target von Hippel - Lindau deficient renal cell carcinoma cells by inducing autophagic cell death

Renal cell carcinomas (RCC) are refractory to standard therapy with advanced RCC having a poor prognosis; consequently treatment of advanced RCC represents an unmet clinical need. The von Hippel-Lindau (VHL) tumor suppressor gene is mutated or inactivated in a majority of RCCs. We recently identified a 4-pyridyl-2-anilinothiazole (PAT) with selective cytotoxicity against VHL-deficient renal cells mediated by induction of autophagy and increased acidification of autolysosomes. We report exploration of structure-activity relationships (SAR) around this PAT lead. Analogues with substituents on each of the three rings, and various linkers between rings, were synthesized and tested in vitro using paired RCC4 cell lines. A contour map describing the relative spatial contributions of different chemical features to potency illustrates a region, adjacent to the pyridyl ring, with potential for further development. Examples probing this domain validated this approach and may provide the opportunity to develop this novel chemotype as a targeted approach to the treatment of RCC. 2009 American Chemical Society.

Strategic studies in the syntheses of novel 6,7-substituted quinolones and 7- or 6-substituted 1,6- and 1,7-naphthyridones

This paper describes the different strategies devised and applied to overcome the selectivity issues in the syntheses of 6,7-disubstituted-1H-quinolin-4-one, 7-substituted-1H-1,6-naphthyridin-4-one and 6-substituted-1H-1,7-naphthyridin-4-one derivatives. They allowed us to improve the overall yields and the scaling-up feasibility. Several examples illustrate these strategies with their advantages and drawbacks.

Preparation of nitropyridines by nitration of pyridines with nitric acid

Preparation of nitropyridines by nitration of pyridines with nitric acid was discussed. Trifluoroacetic anhydride was chilled in an ice bath and the pyridine or substituted pyridines were slowly added and stirred at chilled conditions for 2 h. Relative amounts of the reactants were required for the nitration of pyridine were characterized by 1H and Nuclear magnetic resonance (NMR) spectroscopy and elemental analysis. It was observed that the yields of β-nitropyridines obtained using the standard protocol were generally higher than those obtained using N2O3.

The synthesis of β-nitropyridine compounds

Pyridine and a number of substituted pyridines have been nitrated by reaction with N2O5 followed by reaction with an aqueous solution of SO2xH2O or NaHSO3. The dependence of the yields on the pH of the aqueous reaction medium, on the concentration of SO2xH2O-HSO3-, on addition of methanol to the aqueous phase, and on the reaction temperature were investigated. The yields obtained with NaHSO3 were: 3-nitropyridine 77%, 2-methyl-5-nitro-pyridine 36%, 3-methyl-5-nitropyridinc 24%, 3-acetyl-5-nitropyridine 18%, 5-nitropyridine-3-carboxylic acid 15%, 3-chloro-5-nitropyridine 11%, 4-methyl-3-nitropyridine 39%, 4-acetyl-3-nitropyridine 67%, 4-cyano-3-nitropyridine 45%, 4-phenyl-3-nitropyridine 68%, 4-formyl-3-nitropyridine 62% (from reaction in liquid SO2), 3-nitropyridine-4-carboxylic acid 48%, methyl 3-nitropyridine-4-carboxylate 75%, 2,3-dimethyl-5-nitropyridine 37%, 2,4-dimethyl-5-nitropyridine 64%, 3-nitroquinoline 10% and 4-nitroisoquinoline 42%.