• 1. Distinction of trans–cis photoisomers with comparable optical properties in multiple-state photochromic systems – examining a molecule with three azobenzenes via in situ irradiation NMR spectroscopy?
  Jonas Kind,Lukas Kaltschnee,Martin Leyendecker,Christina M. Thiele Chem. Commun., 2016,52, 12506-12509
• 2. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 3. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 4. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 5. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrroles Pyrrole carboxylic acids and derivatives

Recent Advances in the Application of 4-Bromo-1-methyl-1H-pyrrole-2-carboxylate Ethyl Ester (CAS: 516465-78-4) in Chemical Biology and Pharmaceutical Research

The compound 4-Bromo-1-methyl-1H-pyrrole-2-carboxylate Ethyl Ester (CAS: 516465-78-4) has recently garnered significant attention in chemical biology and pharmaceutical research due to its versatile applications as a key synthetic intermediate. This heterocyclic pyrrole derivative serves as a crucial building block for the development of novel bioactive molecules, particularly in the synthesis of kinase inhibitors and antimicrobial agents. Recent studies have highlighted its role in facilitating efficient C-C and C-N bond formation reactions, enabling the construction of complex molecular architectures with potential therapeutic value.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers demonstrated the compound's utility in the synthesis of pyrrolo[2,3-d]pyrimidine derivatives targeting EGFR tyrosine kinase. The bromo-substitution at the 4-position of the pyrrole ring (516465-78-4) was found to significantly enhance the electrophilic character of the molecule, allowing for efficient palladium-catalyzed cross-coupling reactions. This modification proved critical in developing a new class of anticancer agents with improved selectivity profiles against mutant EGFR isoforms.

Recent advancements in flow chemistry have further expanded the applications of 4-Bromo-1-methyl-1H-pyrrole-2-carboxylate Ethyl Ester. A 2024 Nature Communications paper reported a continuous-flow protocol that significantly improved the yield (up to 92%) and purity (>99%) of downstream products derived from this intermediate. The methodology addressed previous challenges associated with batch processing, particularly in controlling exothermic reactions during large-scale synthesis of pyrrole-containing pharmaceuticals.

The compound's role in antimicrobial drug development has also seen notable progress. Research published in Bioorganic & Medicinal Chemistry Letters (2024) detailed its incorporation into novel pyrrole-azole hybrids exhibiting potent activity against multidrug-resistant Gram-positive pathogens. The ethyl ester moiety in 516465-78-4 was found to enhance membrane permeability while maintaining favorable pharmacokinetic properties, addressing a key limitation in existing antimicrobial scaffolds.

Emerging computational studies have provided deeper insights into the molecular interactions of derivatives stemming from this pyrrole ester. Molecular docking simulations reveal that the bromine atom's strategic positioning creates optimal van der Waals interactions with hydrophobic pockets in target proteins, explaining the enhanced binding affinities observed in several experimental studies. These findings are guiding the rational design of next-generation therapeutic candidates based on this chemical scaffold.

Looking forward, the unique reactivity profile of 4-Bromo-1-methyl-1H-pyrrole-2-carboxylate Ethyl Ester positions it as a valuable tool in fragment-based drug discovery. Its compatibility with modern click chemistry approaches and photoredox catalysis techniques suggests expanding applications in chemical biology probe development and targeted therapeutics. Ongoing research is exploring its potential in PROTAC (proteolysis targeting chimera) design, leveraging the pyrrole core's ability to engage with E3 ubiquitin ligases.

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