Imidazo[1,2-a]pyridin-3-ylacetic acid
[CAS# 17745-04-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Imidazo[1,2-a]pyridin-3-ylacetic acid
• Synonyms: 2-imidazo[1,2-a]pyridin-3-ylacetic acid
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• CAS Registry Number: 17745-04-9
• SMILES: C1=CC2=NC=C(N2C=C1)CC(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.651, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Imidazo[1,2-a]pyridin-3-ylacetic acid is an organic compound that features both an imidazo[1,2-a]pyridine ring system and an acetic acid moiety. This structure imparts unique properties that make it valuable for use in a range of chemical and pharmaceutical applications. The discovery of imidazo[1,2-a]pyridin-3-ylacetic acid is closely tied to the exploration of heterocyclic compounds, specifically those containing fused aromatic systems, which are known for their diverse biological activities and reactivity.

Imidazo[1,2-a]pyridin-3-ylacetic acid can be synthesized through a variety of methods, with a common approach being the functionalization of imidazo[1,2-a]pyridine derivatives. These derivatives are often obtained via nucleophilic substitution reactions, where the imidazo[1,2-a]pyridine core is selectively modified with an acetic acid group. This synthesis allows for precise control over the positioning of functional groups, ensuring the desired reactivity and properties of the final compound.

The chemical structure of imidazo[1,2-a]pyridin-3-ylacetic acid places it at the intersection of two important chemical families: imidazoles and pyridines. These heterocyclic groups are known for their role in biological systems and their ability to interact with a wide variety of receptors and enzymes. The acetic acid moiety further adds to its reactivity, enabling the compound to engage in a variety of chemical transformations.

One of the primary applications of imidazo[1,2-a]pyridin-3-ylacetic acid is in medicinal chemistry. Compounds containing imidazo[1,2-a]pyridine derivatives are known to exhibit a wide range of biological activities, including anti-inflammatory, antiviral, and anticancer properties. In particular, imidazo[1,2-a]pyridin-3-ylacetic acid has been studied for its potential as a therapeutic agent for treating various diseases, including cancer and neurodegenerative disorders. The acetic acid group in the structure can contribute to the solubility and bioavailability of the compound, making it more suitable for pharmacological applications.

In the field of cancer research, imidazo[1,2-a]pyridin-3-ylacetic acid has been explored for its ability to inhibit specific kinases and enzymes that are involved in the progression of cancer. By modulating these biological pathways, compounds like imidazo[1,2-a]pyridin-3-ylacetic acid may help to slow or stop tumor growth. Moreover, the compound's interactions with various cellular targets, including enzymes and receptors involved in inflammation and immune response, make it a candidate for further investigation in autoimmune diseases and inflammatory conditions.

In addition to its medicinal applications, imidazo[1,2-a]pyridin-3-ylacetic acid has potential in materials science. The ability to modify the imidazo[1,2-a]pyridine scaffold allows for the creation of functional materials with specific electronic or optical properties. The compound's versatility in forming derivatives that can be incorporated into organic semiconductors or other functional materials makes it useful for the development of electronic devices, including sensors and light-emitting diodes.

Despite its promising applications, research into imidazo[1,2-a]pyridin-3-ylacetic acid and its derivatives is still ongoing. A key challenge remains optimizing the pharmacokinetic and pharmacodynamic properties of the compound to improve its efficacy and safety in clinical settings. Additionally, efforts are being made to understand its interactions with various biological systems and how these interactions may be leveraged for therapeutic purposes.

In conclusion, imidazo[1,2-a]pyridin-3-ylacetic acid is a valuable chemical compound with significant potential in both medicinal chemistry and materials science. Its structure, featuring both imidazo[1,2-a]pyridine and acetic acid functionalities, allows for a wide range of biological and chemical applications. As research continues, this compound may contribute to the development of new therapies for cancer, neurodegenerative diseases, and inflammatory conditions, as well as advanced materials for electronic applications.

References

1969. Journal of Medicinal Chemistry. , 12(122).

2019. Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum’s Acid. Chemistry of Heterocyclic Compounds, 55.
DOI: 10.1007/s10593-019-02432-6

2007. Novel L-Dopa and Dopamine Prodrugs Containing a 2-Phenyl-imidazopyridine Moiety. Pharmaceutical Research, 24.
DOI: 10.1007/s11095-007-9255-y