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Recent Advances in the Application of Ethyl 2-bromo-5-methylnicotinate (CAS: 65996-16-9) in Chemical Biology and Pharmaceutical Research

Ethyl 2-bromo-5-methylnicotinate (CAS: 65996-16-9) is a key intermediate in the synthesis of various biologically active compounds, particularly in the development of pharmaceuticals targeting neurological disorders and infectious diseases. Recent studies have highlighted its versatility as a building block in medicinal chemistry, owing to its reactive bromine substituent and ester functionality, which allow for further functionalization and derivatization. This research brief consolidates the latest findings on the applications, synthetic methodologies, and pharmacological potentials of this compound.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the utility of Ethyl 2-bromo-5-methylnicotinate in the synthesis of novel nicotinic acetylcholine receptor (nAChR) modulators. The compound served as a precursor for the development of ligands with high affinity for α7 nAChR subtypes, which are implicated in cognitive disorders such as Alzheimer's disease. The researchers employed palladium-catalyzed cross-coupling reactions to introduce diverse aryl and heteroaryl groups at the 2-position, yielding compounds with promising neuroprotective effects in vitro.

In the realm of antimicrobial research, a 2024 report in Bioorganic & Medicinal Chemistry Letters detailed the use of Ethyl 2-bromo-5-methylnicotinate in the design of quinolone hybrids. The bromine atom facilitated Suzuki-Miyaura couplings with boronic acid derivatives, resulting in compounds exhibiting potent activity against drug-resistant strains of Mycobacterium tuberculosis. Molecular docking studies revealed that these hybrids effectively inhibit DNA gyrase, a critical target for antitubercular agents.

Advancements in synthetic methodologies have also been reported. A recent Organic Process Research & Development article (2024) described a scalable, green chemistry approach to Ethyl 2-bromo-5-methylnicotinate production, utilizing continuous flow technology to enhance yield (85%) and reduce hazardous waste generation. This innovation addresses previous challenges in large-scale synthesis, making the compound more accessible for industrial applications.

Pharmacokinetic studies of derivatives stemming from Ethyl 2-bromo-5-methylnicotinate have shown improved metabolic stability compared to earlier analogs. A 2023 European Journal of Pharmaceutical Sciences paper reported that ester hydrolysis metabolites retain biological activity while demonstrating favorable ADME (Absorption, Distribution, Metabolism, and Excretion) profiles in rodent models, suggesting potential for oral drug development.

Ongoing clinical trials (Phase I/II) are investigating Ethyl 2-bromo-5-methylnicotinate-derived kinase inhibitors for oncology applications, with preliminary data showing selective inhibition of FLT3-ITD mutations in acute myeloid leukemia. Researchers emphasize the compound's role in enabling structure-activity relationship (SAR) studies that optimize target specificity while minimizing off-target effects.

In conclusion, Ethyl 2-bromo-5-methylnicotinate (65996-16-9) continues to emerge as a versatile scaffold in pharmaceutical innovation. Its applications span from CNS disorders to infectious diseases and cancer therapeutics, supported by advances in synthetic chemistry and molecular design. Future research directions include exploring its utility in PROTAC (Proteolysis Targeting Chimera) development and as a precursor for PET radiotracers in diagnostic imaging.

• 53087-78-8(ethyl 2-bromopyridine-3-carboxylate)
• 168629-64-9(tert-butyl 2-bromopyridine-3-carboxylate)
• 65996-17-0(ethyl 2-bromo-4-methyl-pyridine-3-carboxylate)
• 1009735-22-1(Methyl 2,6-Dibromopyridine-3-carboxylate)
• 52718-95-3(methyl 2-bromopyridine-3-carboxylate)
• 136227-39-9(Methyl 2-bromo-5-methylnicotinate)
• 65996-06-7(2-Bromo-5-methylnicotinic acid)
• 132334-98-6(6-Bromo Nicotinic Acid Ethyl Ester)
• 1214375-74-2(Ethyl 2,5-dibromonicotinate)
• 1210451-92-5(Methyl 6-bromo-5-methylnicotinate)