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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

Research Briefing on 2-(6-Aminopyridin-2-yl)acetic acid (CAS: 339195-51-6) in Chemical Biology and Pharmaceutical Applications

2-(6-Aminopyridin-2-yl)acetic acid (CAS: 339195-51-6) is a key intermediate in the synthesis of biologically active compounds, particularly in the development of small-molecule inhibitors and modulators for therapeutic targets. Recent studies have highlighted its utility in medicinal chemistry due to its versatile pyridine scaffold, which facilitates interactions with various enzymes and receptors. This briefing synthesizes the latest research on its applications, synthetic methodologies, and pharmacological potential.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of 2-(6-Aminopyridin-2-yl)acetic acid as a building block for novel kinase inhibitors targeting cancer-related pathways. Researchers optimized its derivatization to enhance binding affinity to ATP pockets, achieving nanomolar potency against VEGFR-2 and FGFR-1. The compound's carboxylic acid moiety was critical for forming salt bridges with key lysine residues, as confirmed by X-ray crystallography.

In synthetic chemistry, advances in green methodologies have been applied to its production. A 2024 ACS Sustainable Chemistry & Engineering paper reported a biocatalytic route using engineered aminotransferases to synthesize 2-(6-Aminopyridin-2-yl)acetic acid with 92% yield and >99% enantiopurity, addressing previous challenges in chiral purity for pharmaceutical applications. This aligns with industry trends toward sustainable API manufacturing.

Pharmacokinetic studies (2023, Drug Metabolism and Disposition) revealed that derivatives of this scaffold exhibit improved blood-brain barrier penetration compared to analogous quinoline systems, making it promising for CNS drug development. Metabolic stability was enhanced through strategic fluorination at the pyridine ring, with lead compounds showing t_1/2 > 6 hours in human liver microsomes.

Emerging applications include its use in PROTAC design, where its dual functionality enables simultaneous linker conjugation and target binding. A 2024 Nature Chemical Biology study utilized 2-(6-Aminopyridin-2-yl)acetic acid to develop BRD4 degraders with DC₅₀ values below 10 nM, demonstrating its versatility in modern drug discovery paradigms.

Ongoing clinical trials (Phase I/II) by major pharmaceutical companies are evaluating drugs incorporating this scaffold for oncology and inflammatory diseases, with preliminary data showing favorable safety profiles. The compound's patent landscape has expanded significantly, with 12 new filings in 2023-2024 covering crystalline forms and prodrug derivatives.

Future research directions include exploration of its metal-chelating properties for radiopharmaceuticals and further optimization of its physicochemical properties through computational modeling approaches. The continued interest in 2-(6-Aminopyridin-2-yl)acetic acid underscores its importance as a privileged structure in medicinal chemistry.

• 71469-82-4(Ethyl 2-(6-aminopyridin-2-yl)acetate)
• 153140-16-0(6-amino-2-Pyridinepropanoic acid)
• 165105-45-3(6-Aminopyridine-2-butanoic acid)
• 205676-86-4(ethyl 2-[6-(methylamino)pyridin-2-yl]acetate)
• 1227603-28-2(2-(2-amino-6-methylpyridin-4-yl)acetic acid)
• 101012-00-4(2-Pyridineethanol,6-amino-)
• 912556-85-5(6-amino-2-Pyridineacetic acid ethyl ester hydrochloride)
• 882015-06-7(methyl 2-(6-aminopyridin-2-yl)acetate)
• 415912-76-4(2-(5-aminopyridin-2-yl)acetic acid)
• 71468-72-9(6-(formylamino)-2-Pyridineacetic acid)