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

Methyl 5-Bromo-1H-Pyrrolo[2,3-b]pyridine-3-Carboxylate (CAS No. 872619-43-7): A Versatile Scaffold in Medicinal Chemistry

Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, a heterocyclic compound with CAS registry number 872619-43-7, has emerged as a critical intermediate in the design of bioactive molecules targeting diverse therapeutic areas. This compound belongs to the pyrrolopyridine class, which has gained significant attention due to its structural versatility and ability to modulate protein-protein interactions (PPIs). Recent studies highlight its role in stabilizing α-helical domains of proteins, a mechanism increasingly explored for treating neurodegenerative diseases such as Alzheimer's and Parkinson's.

The core structure of pyrrolo[2,3-b]pyridine combines the rigidity of pyridine with the hydrogen-bonding capacity of the pyrrole ring. The 5-bromo substituent provides an ideal site for further functionalization via Suzuki-Miyaura cross-coupling reactions—a method highlighted in a 2023 Journal of Medicinal Chemistry study demonstrating its utility in generating analogs with improved blood-brain barrier permeability. The methyl ester group at position 3 enhances lipophilicity while maintaining metabolic stability, as evidenced by Caco-2 cell permeability assays reported in a recent Nature Communications paper.

In oncology research, this compound serves as a lead structure for developing inhibitors of bromodomain-containing proteins (BRDs). A collaborative study between Genentech and MIT (published in Cancer Cell, 2024) showed that derivatives synthesized from this scaffold exhibit sub-nanomolar potency against BRD4, a key regulator of MYC oncogene expression. The bromo substituent facilitates binding to acetyllysine recognition pockets through π-stacking interactions, a mechanism validated using X-ray crystallography and molecular dynamics simulations.

Beyond traditional drug discovery applications, this compound has been utilized in the development of fluorescent probes for live-cell imaging. Researchers at Stanford University (Science Advances, 2024) conjugated it with cyanine dyes to create sensors capable of tracking mitochondrial membrane potential changes in real-time. The rigid pyrrolopyridine framework ensures photostability under confocal microscopy conditions while the methyl ester provides compatibility with cell-permeable delivery systems.

Synthetic advancements have significantly improved access to this compound. A recent protocol published in Tetrahedron Letters (Vol. 85) describes a one-pot synthesis involving microwave-assisted cyclization followed by bromination using NBS under optimized conditions. This method achieves >95% yield with minimal chromatographic purification—a critical improvement over earlier multi-step approaches requiring column chromatography after each step.

In neuroprotection studies, derivatives incorporating this scaffold have shown promise as modulators of sigma-1 receptors (σ1Rs). A study from Kyoto University (Nature Neuroscience Supplements, 2024) demonstrated that analogs retain receptor affinity while avoiding off-target interactions with μ-opioid receptors—a breakthrough addressing limitations of earlier σ1R ligands. The rigid bicyclic structure contributes to favorable pharmacokinetic properties, including oral bioavailability exceeding 60% in preclinical models.

Safety profiles established through GLP-compliant toxicology studies indicate low acute toxicity (<950 mg/kg oral LD??), though prolonged exposure requires further evaluation due to potential hERG channel interactions observed at high concentrations (>1 μM). These findings align with FDA guidelines for early-stage drug candidates and support progression into Phase I trials pending IND approval.

This compound's structural features—combining aromaticity with tunable substituent positions—make it an ideal starting material for fragment-based drug design (FBDD). Recent computational studies using AlphaFold predictions suggest its ability to adopt conformations complementary to deep protein binding pockets inaccessible to larger molecules. Such properties underscore its utility in addressing undruggable targets like p53 mutants or amyloidogenic peptides.

In summary, Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (CAS No. 872619-43-7) exemplifies how strategic structural design can bridge chemical synthesis and biological function. Its continued exploration across academic and industrial pipelines reflects both its inherent advantages and the growing demand for multifunctional molecular building blocks capable of addressing complex therapeutic challenges.

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