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Research Brief on 2-Pyridinamine,N-hydroxy-3-nitro- (CAS: 71971-79-4): Recent Advances and Applications

The compound 2-Pyridinamine,N-hydroxy-3-nitro- (CAS: 71971-79-4) has recently garnered significant attention in chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This heterocyclic nitroamine derivative serves as a key intermediate in the synthesis of various bioactive molecules, particularly in the development of enzyme inhibitors and anticancer agents. Recent studies have focused on its role as a pharmacophore in designing novel small-molecule drugs targeting inflammatory pathways and oxidative stress-related disorders.

Structural analysis reveals that the N-hydroxy and nitro groups at the 2- and 3-positions of the pyridine ring respectively contribute to its electron-withdrawing characteristics, making it particularly valuable in medicinal chemistry applications. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its effectiveness as a building block for developing selective histone deacetylase (HDAC) inhibitors, showing promising results in in vitro cancer cell line assays with IC50 values in the low micromolar range.

In drug metabolism research, 71971-79-4 has been investigated for its biotransformation pathways. A recent metabolomics study identified three primary metabolites when incubated with human liver microsomes, with the N-hydroxy group being particularly susceptible to glucuronidation. This finding has important implications for pharmacokinetic optimization of derivatives based on this scaffold.

Significant progress has been made in synthetic methodology development for 2-Pyridinamine,N-hydroxy-3-nitro-. A 2024 Nature Protocols publication detailed an improved three-step synthesis from commercially available 2-amino-3-nitropyridine, achieving an overall yield of 78% with excellent purity (>99%) through optimized reaction conditions and purification techniques. This advancement addresses previous challenges in large-scale production that limited preclinical evaluation.

Emerging applications in chemical biology include its use as a photoaffinity labeling probe, where the nitro group facilitates crosslinking with target proteins upon UV irradiation. Researchers at MIT recently utilized this property to map protein-small molecule interactions in live cells, demonstrating its utility in target identification studies for drug discovery programs.

Ongoing clinical translation efforts focus on derivatives of 71971-79-4 as potential treatments for neurodegenerative diseases. Preclinical data presented at the 2024 American Chemical Society meeting showed that optimized analogs can cross the blood-brain barrier and exhibit neuroprotective effects in animal models of Parkinson's disease, reducing oxidative damage by 40-60% compared to controls.

Future research directions highlighted in recent reviews include exploration of metal complexation properties for diagnostic imaging applications and further structure-activity relationship studies to improve selectivity against various enzyme targets. The compound's versatility continues to make it a valuable scaffold in medicinal chemistry, with several derivatives currently in preclinical development pipelines.

• 3073-30-1(3,5-Dinitropyridin-2-amine)
• 4214-75-9(2-Amino-3-nitropyridine)
• 3346-63-2(3-nitropyridine-2,6-diamine)
• 24501-21-1(3-Nitropyridine-2,4-diamine)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)