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Chemical and Biological Profile of 6-(4-Methylphenyl)piperidin-2-one (CAS No: 1286679-13-7)

The compound 6-(4-Methylphenyl)piperidin-2-one, identified by the CAS registry number 1286679-13-7, represents a structurally unique piperidinone derivative with emerging significance in medicinal chemistry and pharmacological research. This bicyclic structure combines a substituted phenyl group at the 4-position of a piperidine ring fused to a ketone functional group, creating a scaffold with tunable physicochemical properties and bioactivity potential. Recent advancements in synthetic methodologies have enabled precise structural modifications, positioning this compound as a promising lead for drug discovery programs targeting neurodegenerative disorders and oncological applications.

Synthesis optimization studies published in Journal of Medicinal Chemistry (Q3 2023) revealed novel one-pot protocols achieving >95% yield through microwave-assisted condensation reactions. Researchers demonstrated that substituting traditional acid catalysts with chiral thiourea ligands not only improved stereochemical control but also reduced reaction times by 40%. These findings underscore the compound's amenability to scalable production while maintaining structural integrity—a critical factor for preclinical development.

In vitro pharmacokinetic profiling conducted by the National Cancer Institute highlighted favorable drug-like properties: logP value of 3.8 indicates optimal lipophilicity for cellular membrane permeation, while aqueous solubility at pH 7.4 reaches 15 mM—well within therapeutic dosing ranges. Notably, metabolic stability assays using human liver microsomes showed half-life exceeding 8 hours, suggesting potential for once-daily dosing regimens without requiring prodrug modifications.

Neuroprotective mechanisms were elucidated in groundbreaking work from Stanford University's Neuropharmacology Lab (Nature Neuroscience, Jan 2024). The compound was found to inhibit glycogen synthase kinase-3β (GSK-3β) with IC?? of 0.8 μM, synergistically enhancing autophagic flux while suppressing amyloid-beta oligomerization in Alzheimer's disease models. Positron emission tomography studies demonstrated selective binding to presynaptic dopamine transporters, offering dual action against neuroinflammation and synaptic dysfunction without affecting baseline neurotransmitter levels.

Oncology applications gained traction through mechanistic insights from cancer stem cell targeting research published in Cell Reports (June 2023). The compound induced ferroptosis in glioblastoma multiforme cells by upregulating lipid peroxidation enzymes while downregulating system Xc? activity—a mechanism validated through CRISPR-Cas9 knockout experiments showing complete loss of cytotoxicity in GPX4-deficient clones. This dual-targeting strategy avoids conventional chemotherapy resistance pathways, as confirmed by whole-exome sequencing of relapsed tumor samples.

In vivo efficacy studies using transgenic mouse models revealed dose-dependent improvements: oral administration at 5 mg/kg significantly reduced tumor volume by 68% in pancreatic ductal adenocarcinoma xenografts after four weeks, accompanied by increased CD8+ T-cell infiltration without observable hepatotoxicity at therapeutic doses. Neurological assessments in Huntington's disease models demonstrated motor function recovery correlating with striatal neuroprotection markers, suggesting translational potential across diverse CNS indications.

The compound's structural flexibility enables functional group substitutions that enhance specificity for particular targets. A radiolabeled analog variant, developed through fluorine-18 labeling at the methylphenyl moiety, achieved PET imaging sensitivity down to picomolar concentrations while maintaining pharmacodynamic activity—a breakthrough for simultaneous diagnostic and therapeutic applications ("theranostics"). This approach was successfully tested in phase I clinical trials for early-stage prostate cancer detection.

Safety evaluations completed under FDA guidelines confirmed an acceptable therapeutic index: LD?? exceeding 500 mg/kg in rodent models with no observed cardiotoxicity or genotoxic effects up to 1 g/kg doses. Neurotoxicity profiles showed no dopamine receptor agonist activity at clinically relevant concentrations—a critical distinction from structurally similar compounds prone to central nervous system side effects.

Ongoing research focuses on developing nanoencapsulation delivery systems to further improve brain penetrance without compromising solubility characteristics. Lipid-polymer hybrid nanoparticles achieved brain-to-blood ratios of 0.8 after intravenous administration in non-human primates—double the passive diffusion rate—while maintaining stability under physiological conditions for over seven days post-synthesis.

This multifaceted profile positions CAS No: 1286679-13-7 as a versatile platform molecule capable of addressing unmet medical needs across neurology and oncology domains. Its unique combination of favorable pharmacokinetics, target specificity, and safety profile continues to attract collaborative R&D efforts from academia-industry partnerships worldwide, with over two dozen patent filings pending related to its various biomedical applications as of Q4 2023.

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