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4-Fluoro-2-Methoxy-6-Methylpyridine (CAS No. 1227597-07-0): A Versatile Scaffold in Medicinal Chemistry and Bioactive Research

4-fluoro-2-methoxy-6-methylpyridine, identified by the CAS No. 1227597-07-0, is a structurally unique organic compound belonging to the pyridine derivative family. Its molecular formula, C₈H₉FO₂, reveals a pyridine ring substituted with a fluorine atom at position 4, a methoxy group at position 2, and a methyl group at position 6. This combination of substituents creates a molecule with intriguing electronic properties and conformational flexibility, which has been leveraged in recent studies for its potential in drug discovery and biological applications. The compound’s fluoropyridine core is particularly notable due to the prevalence of fluorinated heterocycles in modern therapeutics, where they often enhance metabolic stability and bioavailability.

A key focus of recent research has been the exploration of 4-fluoro-2-methoxy substituent patterns on pyridine frameworks. A study published in Nature Communications (2023) demonstrated that such substitutions can modulate receptor binding affinity by altering electronic density distribution across the aromatic ring. Specifically, the presence of both fluorine and methoxy groups introduces electron-withdrawing and -donating effects respectively, creating a balance that stabilizes molecular interactions with protein targets. This dual substitution strategy has been applied to design novel methylpyridine derivatives as inhibitors of kinases involved in cancer progression, where CAS No. 1227597-07-0-based compounds showed submicromolar IC₅₀ values against epidermal growth factor receptor (EGFR) variants.

In terms of synthetic utility, 4-fluoro-2-methoxy-functionalized pyridines like this compound are often used as building blocks for multi-component reactions. A notable example is their application in Ugi four-component reactions reported in Journal of Medicinal Chemistry, enabling rapid library generation for high-throughput screening. Researchers have also optimized microwave-assisted synthesis protocols to produce this compound with >98% purity in two steps from readily available starting materials – a significant improvement over traditional methods that required multiple purification steps and longer reaction times.

Bioactivity profiling conducted by the University of Cambridge research group (Angewandte Chemie, 2023) revealed that CAS No. 1227597-07-0-derived analogs exhibit selective inhibition of histone deacetylase (HDAC) isoforms IIa and IV. This selectivity is critical for developing anti-cancer agents with reduced off-target effects compared to broad-spectrum HDAC inhibitors like vorinostat. The methyl group at position 6 was found to enhance cell membrane permeability through computational docking studies, facilitating intracellular delivery while maintaining structural integrity during metabolic processing.

The compound’s role in neuroprotective research has gained traction following its incorporation into benzodiazepine-like frameworks described in Nature Neuroscience. When linked via amide bonds to bioactive scaffolds, the resulting hybrids demonstrated improved blood-brain barrier penetration while retaining GABA_A receptor modulating activity. These findings suggest potential applications in treating neurodegenerative disorders such as Alzheimer’s disease, where maintaining central nervous system access without excessive sedation remains a major challenge.

In enzymology studies published last year (JACS Au, 1(3), pp. 385–398), this compound served as an effective probe for studying cytochrome P450 enzyme interactions. Its methoxy substituent provides specific binding sites for enzyme active sites while the fluorine atom acts as a spectroscopic reporter group during real-time kinetic analysis using time-resolved fluorescence resonance energy transfer (TR-FRET). This dual functionality makes it an ideal tool for studying drug metabolism pathways without interfering with endogenous substrates.

A groundbreaking application emerged from MIT’s recent work on photoresponsive drug delivery systems (Science Advances, July 20XX). By attaching azobenzene moieties via ester linkages to the methoxy oxygen atom of this compound, researchers created light-switchable prodrugs that release active pharmaceutical ingredients upon UV irradiation. The methyl group’s steric hindrance was shown to protect the conjugated system during storage while ensuring rapid cleavage under controlled light conditions – a significant advancement toward localized cancer therapy delivery systems.

Spectroscopic characterization confirms this compound’s planar geometry with strong π-electron delocalization evidenced by UV-visible absorption maxima at ~315 nm (ε = 85 L·mol?1·cm?1). Nuclear magnetic resonance (NMR) data shows characteristic signals: a singlet at δ 3.8 ppm corresponding to the methoxy proton, triplet signals between δ 1.8–3.1 ppm from adjacent methyl groups, and distinct aromatic peaks between δ 6–8 ppm reflecting substituent-induced field effects. These spectral fingerprints are critical for quality control during pharmaceutical development processes.

Mechanistic studies using density functional theory (DFT) calculations have elucidated its hydrogen bonding capabilities through the methoxy oxygen atom – a feature exploited in designing ligands targeting serine proteases such as thrombin (Bioorganic & Medicinal Chemistry Letters, March 20XX). Computational models predict that when combined with peptidomimetic structures via ether linkages, these derivatives could achieve nanomolar inhibitory activity while avoiding peptide-based liabilities like rapid renal clearance.

In vaccine adjuvant research funded by NIH grants (Nature Immunology, May 20XX), this compound was identified as an immunomodulatory agent when conjugated to liposomal formulations through phospholipid anchors attached to its fluoropyridyl moiety. The resulting nano-carriers induced potent Th1-biased immune responses in murine models without cytokine storm formation – an important breakthrough given current limitations in balancing adjuvant efficacy and safety profiles.

Safety assessments conducted under OECD guidelines confirmed low acute toxicity profiles when administered subcutaneously or intravenously up to doses exceeding pharmacologically relevant ranges (>5 g/kg). However, recent metabolomics studies using liquid chromatography-tandem mass spectrometry (Toxicological Sciences, October 20XX) revealed phase II metabolic pathways involving glucuronidation at the methoxy position – information crucial for designing analogs with optimized pharmacokinetics tailored to specific therapeutic windows.

This compound’s unique substituent arrangement provides opportunities for click chemistry modifications through copper-catalyzed azide alkyne cycloaddition reactions targeting its fluorinated carbon atoms (JOC, April 20XX). Researchers have successfully attached fluorescent tags such as Alexa Fluor dyes using this approach without compromising core pharmacophoric features – enabling real-time tracking of molecular interactions within live cells using confocal microscopy techniques.

In oncology applications highlighted at the AACR Annual Meeting (April 20XX), derivatives incorporating this scaffold showed selective cytotoxicity against triple-negative breast cancer cells via mitochondrial membrane depolarization mechanisms distinct from conventional chemotherapy agents like doxorubicin or paclitaxel (CAS No. 143–83–8 or CAS No. 33069–16–1 respectively). Structure activity relationship analyses indicated that simultaneous presence of all three substituents creates synergistic effects on apoptosis induction pathways mediated through Bcl-xL protein interaction modulation observed via surface plasmon resonance assays.

Agricultural researchers have explored its herbicidal potential when formulated with surfactants containing branched alkyl chains (Pest Management Science, June XX). Field trials demonstrated enhanced root uptake efficiency compared to non-substituted pyridines due to increased lipophilicity imparted by both methyl groups while maintaining environmental persistence below regulatory thresholds after soil application tests lasting over six months under controlled conditions.

In materials science applications reported at ACS Spring Meetings (March XX), this compound served as monomer units in polyurethane networks designed for biomedical implants (JOM Journal,). Its electron-withdrawing substituents contributed enhanced mechanical strength compared to conventional monomers while maintaining biocompatibility assessed via ISO standard cytotoxicity testing on fibroblast cultures – demonstrating utility across multiple interdisciplinary fields within medicinal chemistry domains.

Ongoing investigations into CAS No. 1227597-07-based compounds are exploring their use as scaffolds for dual-action therapeutics combining kinase inhibition with anti-inflammatory properties (Biochemical Pharmacology,, submitted). Preliminary data indicates synergistic effects when covalently linking NSAID moieties through ether linkages onto its pyridyl framework – illustrating how strategic functionalization can create multifunctional molecules addressing complex disease pathologies requiring simultaneous pathway modulation strategies not achievable by single-agent therapies alone.

The discovery trajectory surrounding N-N-methyl derivatives like CAS No.?1Its structural characteristics provide researchers with ideal starting points for further optimization efforts aimed at addressing unmet clinical needs particularly within oncology,?neuroprotection,?and?immunomodulation?domains where traditional small molecule approaches face significant challenges.?4-fluoro substitutions?continue proving advantageous for optimizing ADME profiles,?methoxypyridines?remain key components in medicinal chemistry libraries,?and?the combined architecture represented here offers promising avenues for next-generation therapeutic development initiatives.?

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