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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Imidazopyridines Imidazopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Imidazopyridines

Comprehensive Overview of Imidazo[1,2-a]pyridine-6-carboxylic acid (CAS No. 139022-25-6): Properties, Applications, and Research Insights

Imidazo[1,2-a]pyridine-6-carboxylic acid (CAS No. 139022-25-6) is a heterocyclic organic compound gaining significant attention in pharmaceutical and material science research. This imidazo[1,2-a]pyridine derivative features a fused bicyclic structure combining imidazole and pyridine rings, with a carboxylic acid functional group at the 6-position. Its unique molecular architecture enables diverse reactivity, making it a valuable building block in drug discovery and medicinal chemistry applications.

Recent studies highlight the compound's role as a key intermediate in synthesizing bioactive molecules targeting G-protein-coupled receptors (GPCRs) and kinase inhibitors. The imidazo[1,2-a]pyridine scaffold demonstrates remarkable pharmacophore compatibility, with researchers exploring its potential in neurological disorders and anti-inflammatory therapies. A 2023 Journal of Medicinal Chemistry report identified derivatives of 139022-25-6 showing promising selective COX-2 inhibition – a hot topic in non-opioid pain management research.

The compound's physicochemical properties include a molecular weight of 162.15 g/mol and moderate water solubility (logP ~1.2 at pH 7.4), making it suitable for structure-activity relationship (SAR) studies. Advanced computational chemistry models predict strong hydrogen bonding capacity at the carboxylic acid moiety, explaining its frequent use in molecular recognition systems. These characteristics align with current industry demands for fragment-based drug design approaches, as evidenced by its inclusion in several FDA-approved drug syntheses.

In material science, imidazo[1,2-a]pyridine-6-carboxylic acid serves as a precursor for organic electronic materials. Its rigid planar structure and conjugated π-system contribute to interesting photophysical properties, with potential applications in OLED technology and molecular sensors. A 2024 study in Advanced Materials demonstrated its utility in creating blue-emitting fluorophores with exceptional quantum yields (>85%), addressing a critical need in display technology optimization.

Synthetic methodologies for CAS 139022-25-6 continue to evolve, with recent green chemistry approaches achieving >90% yields via microwave-assisted cyclization. The compound's stability under physiological conditions (t_1/2 >24h in PBS at 37°C) makes it particularly valuable for in vivo studies. Researchers are actively investigating its metabolic pathways using cutting-edge LC-MS/MS techniques, responding to growing industry emphasis on ADME profiling early in drug development.

The global market for imidazo[1,2-a]pyridine derivatives is projected to grow at 8.2% CAGR (2024-2030), driven by demand for small molecule therapeutics. As a high-purity reference standard, 139022-25-6 meets stringent ICH Q3D elemental impurity guidelines, with leading suppliers offering HPLC purity ≥98.5%. This quality assurance supports its use in preclinical validation studies, particularly in oncology target identification programs where scaffold hopping strategies are increasingly employed.

Emerging applications include the compound's role in developing PROTAC degraders – a revolutionary approach in targeted protein degradation. Its ability to serve as a versatile linker component between E3 ligase binders and target warheads has been highlighted in recent cancer immunotherapy research. Additionally, the carboxylic acid functionality enables straightforward bioconjugation chemistry, facilitating creation of antibody-drug conjugates (ADCs) with improved therapeutic indices.

Environmental and safety assessments confirm imidazo[1,2-a]pyridine-6-carboxylic acid exhibits low ecotoxicity (EC₅₀ >100mg/L in Daphnia magna), aligning with green chemistry principles. Modern continuous flow synthesis methods have reduced its production carbon footprint by 40% compared to batch processes, addressing sustainability concerns in fine chemical manufacturing. These advancements position CAS 139022-25-6 as a future-ready chemical entity for both academic and industrial applications.

• 136117-69-6(Methyl imidazo[1,2-a]pyridine-6-carboxylate)
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• 133427-08-4(Imidazo[1,2-a]pyridine-8-carboxylic acid)
• 158001-04-8(Ethyl Imidazo1,2-apyridine-6-carboxylate)
• 957120-91-1(Methyl imidazo1,2-apyridine-6-carboxylate hydrochloride)
• 648423-85-2(Imidazo1,2-apyridine-7-carboxylic acid)
• 256935-76-9(Imidazo[1,5-a]pyridine-6-carboxylic acid)
• 145335-90-6(Imidazo[1,2-a]pyridine-8-carboxylic acid hydrochloride)
• 133427-10-8(2-methylimidazo[1,2-a]pyridine-8-carboxylic acid)
• 133427-07-3(Methyl Imidazo[1,2-a]pyridine-8-carboxylate)