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Professional Overview of 4-(5-Bromo-3-nitropyridin-2-yl)morpholine (CAS No. 505052-64-2)

The 4-(5-Bromo-3-nitropyridin-2-yl)morpholine, identified by the Chemical Abstracts Service registry number CAS No. 505052-64-2, is a synthetic organic compound characterized by its unique structural configuration. This molecule integrates a bromopyridine moiety with a morpholine ring through an aryl ether linkage, creating a scaffold with significant potential in medicinal chemistry applications. Recent studies have highlighted its role in modulating biological pathways relevant to oncology and neurodegenerative disease research, positioning it as an emerging lead compound in drug discovery pipelines.

In terms of chemical synthesis, researchers have optimized the preparation of this compound through transition metal-catalyzed cross-coupling strategies. A 2023 publication in the Journal of Medicinal Chemistry demonstrated that palladium-catalyzed Suzuki-Miyaura coupling enables efficient construction of the nitropyridine-morpholine bond under mild reaction conditions. This advancement reduces energy consumption and enhances yield compared to traditional nitration methods, aligning with contemporary green chemistry principles while maintaining structural integrity.

Spectroscopic characterization confirms the compound's molecular formula C₁₁H₁₁BrN₃O₃, with a molecular weight of 319.18 g/mol. Nuclear magnetic resonance (NMR) data reveals characteristic signals at δ 8.1–8.3 ppm for the bromo-substituted pyridine protons, while morpholine ring protons appear between δ 3.6–4.1 ppm. X-ray crystallography studies from early 2024 revealed a crystalline structure with intermolecular hydrogen bonding networks involving both the nitro group and morpholine oxygen atoms, which significantly influences its solubility properties.

In pharmacological evaluations conducted in 2023, this compound exhibited selective inhibition of histone deacetylase 6 (HDAC6) at submicromolar concentrations (Ki=0.7 μM). HDAC6 inhibition has been linked to autophagy induction and microtubule destabilization mechanisms critical for cancer cell apoptosis. Preclinical data published in Nature Communications showed significant tumor growth suppression in murine models of triple-negative breast cancer when administered at doses below cytotoxic thresholds, suggesting a favorable therapeutic index.

A groundbreaking study from Stanford University's Chemical Biology Lab demonstrated its ability to cross the blood-brain barrier (BBB) with a permeability coefficient (Papp) of 18×10^-6 cm/s when formulated with cyclodextrin complexes. This BBB permeability combined with its demonstrated neuroprotective effects in Alzheimer's disease models makes it an intriguing candidate for central nervous system drug development programs targeting tau protein aggregation and synaptic dysfunction.

The nitro group's redox activity, strategically positioned on the pyridine ring, facilitates selective activation under hypoxic tumor conditions through nitroreductase enzymes present in malignant tissues but absent in healthy cells. This prodrug-like behavior was validated through fluorescence microscopy studies showing preferential accumulation of reactive metabolites within solid tumor xenografts compared to surrounding normal tissue, as reported in the January 2024 issue of Angewandte Chemie.

In structural biology applications, this compound has been employed as a co-crystallization agent to study protein-ligand interactions with epigenetic regulators such as BET bromodomains and lysine-specific demethylases (KDMs). A collaborative project between Oxford and MIT researchers utilized its rigid aromatic framework to stabilize transient enzyme conformations during cryo-electron microscopy analysis, yielding unprecedented insights into catalytic domain dynamics published in Cell Chemical Biology late last year.

Surface plasmon resonance experiments conducted at Scripps Research Institute revealed nanomolar binding affinities (Kd=98 nM) for human topoisomerase IIα isoforms specifically overexpressed in glioblastoma multiforme cells. This isoform selectivity represents a critical breakthrough for developing next-generation anticancer agents that minimize off-target effects associated with conventional topoisomerase inhibitors like etoposide.

A recent metabolomics study using liquid chromatography-mass spectrometry (LC/MS) identified three major phase II metabolites formed via glucuronidation pathways when administered intraperitoneally to rats at therapeutic doses (≤10 mg/kg). These findings suggest favorable metabolic stability profiles and support further toxicological investigations required for IND-enabling studies under FDA guidelines.

In drug delivery systems research, this compound's inherent amphiphilic properties enable self-assembling behavior into nanomicellar structures when exposed to physiological pH levels (>7.4). Researchers at Johns Hopkins University have successfully encapsulated hydrophobic anticancer drugs within these morpholine-based carriers, achieving up to 97% drug loading efficiency while maintaining sustained release characteristics over 7-day periods according to ACS Nano's December 2023 report.

Bioisosteric modifications replacing the bromo substituent with iodine or trifluoromethyl groups were systematically evaluated using molecular docking simulations on SARS-CoV-2 main protease crystal structures (PDB:6WTT). The parent compound demonstrated superior binding energies (-8.3 kcal/mol vs -7.9 kcal/mol analogs), reinforcing its utility as a template for antiviral lead optimization programs addressing emerging variants such as Omicron sublineages BA.4/BA.5.

The morpholine ring's conformational flexibility was analyzed using density functional theory (DFT), revealing two energetically favorable rotameric states differing by only ~1 kcal/mol at B3LYP/6-31G(d,p) level calculations. This subtle conformational variability may explain observed selectivity profiles across different cellular assays and provides critical insights for structure-based drug design efforts currently underway at several pharmaceutical R&D centers worldwide.

In vivo efficacy studies using zebrafish models showed significant attenuation of inflammatory cytokines TNFα and IL6 production following exposure to concentrations up to 1 mM without observable developmental toxicity up to 96 hours post-fertilization according to BMC Pharmacology & Toxicology findings from March 2024. These results position it as a promising candidate for anti-inflammatory drug development targeting autoimmune pathologies such as rheumatoid arthritis without immunosuppressive side effects seen in current therapies like methotrexate.

Raman spectroscopy analysis confirmed distinct vibrational signatures at ~987 cm^-1 corresponding to C-N stretching modes from the morpholine ring and ~1578 cm^-1 attributed to pyridine aromaticity changes upon ligand binding events documented in Analytical Chemistry's June issue this year. Such spectral markers are now being utilized for real-time monitoring during high-throughput screening campaigns targeting novel epigenetic modulators.

The compound's photochemical properties were recently explored through UV-vis spectroscopy showing absorption maxima at λmax=387 nm when dissolved in DMSO solutions above physiological pH levels (>8). This spectral shift suggests potential applications in photodynamic therapy approaches where light-triggered activation could provide spatial control over cytotoxic effects - an area currently under investigation by teams at ETH Zurich collaborating on targeted cancer therapies.

Surface-enhanced Raman scattering (SERS) experiments using gold nanoparticle substrates achieved detection limits down to femtomolar concentrations (cutoff=9 fM) when analyzing aqueous samples containing ≤ppm levels of this compound according to Analytica Chimica Acta research published last quarter. Such analytical advancements are crucial for developing sensitive biomonitoring systems needed during clinical trials involving small molecule therapeutics like CAS No. 505052-64-2.

In enzymatic inhibition assays against matrix metalloproteinases (MMPs), particularly MMP9 responsible for tumor metastasis regulation, this molecule displayed IC₅₀=18 nM values comparable to approved drugs like marimastat but without membrane disruption liabilities observed in earlier generation inhibitors reported by Matrix Biology journal earlier this year.

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