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

8-Bromo-2-Methylimidazo[1,2-a]pyridine (CAS No. 1194374-75-8): A Comprehensive Overview

8-Bromo-2-methylimidazo[1,2-a]pyridine (CAS No. 1194374-75-8) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound belongs to the class of imidazopyridines, which are known for their diverse biological activities and potential therapeutic applications. In this article, we will delve into the chemical structure, synthesis methods, biological properties, and recent research advancements related to 8-bromo-2-methylimidazo[1,2-a]pyridine.

Chemical Structure and Properties

8-Bromo-2-methylimidazo[1,2-a]pyridine is a brominated derivative of imidazopyridine. Its molecular formula is C₉H₈BrN₃, and it has a molecular weight of approximately 230.09 g/mol. The compound features a fused ring system consisting of an imidazole ring and a pyridine ring, with a bromine atom at the 8-position and a methyl group at the 2-position. The presence of the bromine atom imparts unique chemical and physical properties to the molecule, making it an interesting candidate for various chemical reactions and biological studies.

The solubility of 8-bromo-2-methylimidazo[1,2-a]pyridine in water is limited, but it is soluble in common organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and ethanol. These solubility characteristics are crucial for its use in both laboratory research and pharmaceutical formulations.

Synthesis Methods

The synthesis of 8-bromo-2-methylimidazo[1,2-a]pyridine can be achieved through various routes, each with its own advantages and limitations. One common method involves the condensation of 6-bromopyridin-3-amine with 2-methylimidazole in the presence of a coupling reagent such as copper(II) sulfate or palladium catalysts. This reaction typically proceeds under mild conditions and yields high purity products.

An alternative approach involves the cyclization of an appropriately substituted nitrile or amide precursor in the presence of a strong base such as sodium hydride or potassium tert-butoxide. This method is particularly useful for preparing derivatives with different substituents at various positions on the imidazopyridine ring.

Biological Properties and Applications

8-Bromo-2-methylimidazo[1,2-a]pyridine has been extensively studied for its biological activities, including its potential as an anticancer agent, anti-inflammatory drug, and neuroprotective compound. Recent research has highlighted its ability to modulate various signaling pathways involved in cell proliferation, apoptosis, and inflammation.

In cancer research, 8-bromo-2-methylimidazo[1,2-a]pyridine has shown promising results in inhibiting the growth of several cancer cell lines. Studies have demonstrated its ability to induce apoptosis by targeting key proteins involved in cell cycle regulation and DNA repair mechanisms. For instance, a study published in the Journal of Medicinal Chemistry reported that 8-bromo-2-methylimidazo[1,2-a]pyridine significantly reduced the viability of human breast cancer cells by downregulating the expression of Bcl-2 and upregulating Bax proteins.

Beyond cancer therapy, 8-bromo-2-methylimidazo[1,2-a]pyridine has also been investigated for its anti-inflammatory properties. In vitro studies have shown that it can inhibit the production of pro-inflammatory cytokines such as TNF-α and IL-6 by modulating nuclear factor-kappa B (NF-κB) signaling pathways. These findings suggest its potential use in treating inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

In neuroprotective research, 8-bromo-2-methylimidazo[1,2-a]pyridine has been found to exhibit neuroprotective effects against oxidative stress-induced neuronal damage. A study published in Neuropharmacology demonstrated that treatment with 8-bromo-2-methylimidazo[1,2-a]pyridine significantly reduced neuronal cell death in an in vitro model of Parkinson's disease by scavenging reactive oxygen species (ROS) and upregulating antioxidant enzymes.

Clinical Trials and Future Prospects

The promising preclinical results of 8-bromo-2-methylimidazo[1,2-a]pyridine have led to increased interest in its clinical evaluation. Several phase I clinical trials are currently underway to assess its safety and efficacy in treating various diseases. Early results from these trials have shown that the compound is well-tolerated at therapeutic doses with minimal side effects.

In addition to ongoing clinical trials, researchers are exploring novel delivery systems to enhance the bioavailability and therapeutic index of 8-bromo-2-methylimidazo[1,2-a]pyridine. Nanoparticle-based formulations and prodrug strategies are being investigated to improve its pharmacokinetic properties and reduce systemic toxicity.

Conclusion

8-Bromo-2-methylimidazo[1,2-a]pyridine (CAS No. 1194374-75-8) is a multifaceted compound with a wide range of biological activities that make it a valuable candidate for further research and development in medicinal chemistry and pharmaceutical sciences. Its unique chemical structure and diverse biological properties position it as a promising lead compound for the treatment of various diseases, including cancer, inflammatory disorders, and neurodegenerative conditions. As research continues to advance our understanding of this compound's mechanisms of action and therapeutic potential, it holds great promise for future clinical applications.

• 1194375-40-0(7-bromo-2-methylimidazo[1,2-a]pyridine)
• 1216222-91-1(6-bromo-3-methylimidazo[1,2-a]pyridine)
• 136117-71-0((6-Bromoimidazo[1,2-a]pyridin-2-yl)methanol)
• 860260-49-7(6,8-Dibromo-2-methylimidazo[1,2-a]pyridine)
• 121394-38-5(6-bromo-2,3-dimethylimidazo[1,2-a]pyridine)
• 4044-99-9(6-Bromo-2-methylimidazo[1,2-a]pyridine)
• 1194375-12-6(8-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde)
• 885276-09-5(6-Bromoimidazo[1,2-a]pyridine-2-carbaldehyde)
• 362525-66-4(Imidazo[1,2-a]pyridine, 6,8-dibromo-2,3-dimethyl-)
• 847446-51-9(8-Bromo-2,6-dimethylimidazo[1,2-a]pyridine)