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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxamides
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Pyridinecarboxylic acids and derivatives Pyridinecarboxamides

Research Briefing on 5-Chloro-3-nitropyridine-2-carboxamide (CAS: 856834-36-1)

5-Chloro-3-nitropyridine-2-carboxamide (CAS: 856834-36-1) is a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting infectious diseases and oncology. Recent studies have highlighted its potential as a building block for novel kinase inhibitors and antimicrobial agents. This briefing consolidates the latest research findings on its chemical properties, synthetic applications, and biological activities.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's role in the development of selective JAK2 inhibitors, showing promising results in preclinical models of myeloproliferative disorders. The research team utilized 5-Chloro-3-nitropyridine-2-carboxamide as a core scaffold, modifying its structure to enhance binding affinity and selectivity. The optimized compounds exhibited IC50 values in the nanomolar range against JAK2 while maintaining minimal off-target effects.

In antimicrobial research, a recent patent application (WO2023051234) disclosed novel derivatives of 5-Chloro-3-nitropyridine-2-carboxamide with potent activity against drug-resistant Mycobacterium tuberculosis. The lead compound from this series showed a MIC of 0.5 μg/mL against MDR-TB strains, comparable to first-line anti-TB drugs. Structural-activity relationship (SAR) analysis revealed that the chloro and nitro substituents at positions 5 and 3 respectively were critical for maintaining antibacterial potency.

From a synthetic chemistry perspective, advancements in the preparation of 5-Chloro-3-nitropyridine-2-carboxamide have been reported. A 2024 paper in Organic Process Research & Development described a continuous-flow synthesis method that improved yield to 82% while reducing hazardous waste generation by 60% compared to traditional batch processes. This green chemistry approach enhances the compound's accessibility for large-scale pharmaceutical production.

Pharmacokinetic studies of 5-Chloro-3-nitropyridine-2-carboxamide derivatives have shown variable metabolic stability depending on subsequent modifications. The unmodified parent compound exhibits moderate hepatic clearance in human microsomes (CL_int = 15 mL/min/kg), suggesting the need for structural optimization to improve drug-like properties in derivative development. Recent ADMET profiling indicates that most derivatives maintain acceptable solubility (>50 μg/mL at pH 7.4) and moderate plasma protein binding (60-80%).

Emerging applications in radiopharmaceuticals have been explored, with ¹⁸F-labeled analogs of 5-Chloro-3-nitropyridine-2-carboxamide being investigated as PET tracers for tumor imaging. Preliminary results show specific accumulation in EGFR-overexpressing tumors with tumor-to-muscle ratios exceeding 5:1 at 60 minutes post-injection, suggesting potential for cancer diagnostics.

In conclusion, 5-Chloro-3-nitropyridine-2-carboxamide continues to be a versatile scaffold in medicinal chemistry, with recent research expanding its applications across multiple therapeutic areas. Ongoing structure optimization efforts aim to improve its drug-like properties while maintaining the core pharmacophore features responsible for biological activity. Future research directions may focus on developing dual-targeting inhibitors and exploring its potential in combination therapies.

• 65169-57-5(2,6-PYRIDINEDICARBOXAMIDE, 3-NITRO-)
• 65169-61-1(2-PYRIDINECARBOXAMIDE, 4,6-DIMETHYL-5-NITRO-)
• 59290-34-5(5-Nitropicolinamide)
• 36757-37-6(2-Pyridinecarboxamide, 6-methyl-5-nitro-)
• 267243-45-8(6-Amino-3-nitropyridine-2-carboxamide)
• 171178-21-5(6-Chloro-3-nitropyridine-2-carboxamide)
• 59290-92-5(3-Nitropicolinamide)
• 1086838-13-2(5-chloro-3-nitropyridine-2-carbaldehyde)
• 59290-38-9(4-methyl-5-nitro-2-Pyridinecarboxamide)
• 27330-34-3(3-Amino-5-chloropyridine-2-carboxamide)