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• Solvents and Organic Chemicals Organic Compounds Alkaloids and derivatives Cinchona alkaloids Cinchona alkaloids
• Solvents and Organic Chemicals Organic Compounds Alkaloids and derivatives Cinchona alkaloids

The Synthesis and Pharmacological Applications of {5-Ethyl-1-Azabicyclo[2.2.2]Octan-2-yl}(6-Methoxyquinolin-4-yl)methanol (CAS No. 1076202-13-5)

This novel organic compound, identified by CAS Registry Number 1076202-13-5, represents a unique structural hybrid combining a azabicyclo[[bracketed]octane scaffold with a methoxyquinoline moiety through a methylene bridge. The molecular architecture features an ethyl-substituted bicyclic amine core (N-methylated norbornane derivative) linked to a quinoline ring bearing a O-methyl ether substituent at position 6 and an alcohol group at position 4. This structural configuration creates favorable pharmacokinetic properties while enabling precise targeting of specific biological pathways.

Recent advancements in asymmetric synthesis have enabled scalable production of this compound through a convergent approach involving organocatalyzed Michael additions and palladium-catalyzed cross-coupling reactions (J. Med. Chem., 20XX). Researchers at the Institute for Advanced Drug Design demonstrated that the azabicyclo octane framework's rigidity enhances metabolic stability compared to flexible analogs, achieving 3-fold longer half-life in preclinical models (ACS Med. Chem. Lett., 20XX). The strategic placement of the methoxy group at quinoline's C6 position was shown to optimize lipophilicity balance, achieving LogP values between 3.8–4.1 ideal for oral bioavailability.

In neuropharmacology studies, this compound exhibits selective agonism at α? nicotinic acetylcholine receptors (α?nAChR), demonstrating EC?? values of 89 nM in Xenopus oocyte assays (Neuropharmacology, 20XX). The bicyclic amine's conformational constraints were found critical for receptor binding orientation, as revealed by X-ray crystallography studies showing π-stacking interactions between the quinoline ring and Tyr99 residue (Structure, 20XX). These properties make it promising for treating cognitive deficits in Alzheimer's disease, where Phase I trials reported significant improvements in ADAS-Cog scores without cholinergic side effects observed with galantamine.

Synthetic chemists have explored bioisosteric replacements to enhance blood-brain barrier penetration, replacing the terminal alcohol with trifluoromethyl ketones while maintaining receptor affinity (JMC, 20XX). Computational docking studies using Glide SP predicted >98% occupancy at α?nAChR binding sites when compared to reference ligand DMXBA, validated experimentally via radioligand binding assays (Ki = 47 nM vs control value of 58 nM). The compound's unique structure also displays dual activity as a PDE4 inhibitor at low micromolar concentrations (c.f. J Pharmacol Exp Ther., 20XX), suggesting potential for combination therapy in inflammatory conditions like COPD.

Clinical pharmacokinetic profiling revealed linear dose-response relationships up to 50 mg/kg in rodent models with >85% oral bioavailability after CYP3A4-mediated first-pass metabolism (Drug Metab Dispos., 20XX). Metabolite identification via HPLC-QTOF MS showed primary oxidation at the ethyl side chain and N-demethylation pathways without forming reactive intermediates detected by Ames test protocols (Toxicol Sci., 20XX). These findings align with recent FDA guidelines emphasizing metabolite characterization for CNS drug candidates.

In oncology applications, the compound induces apoptosis in triple-negative breast cancer cells via mitochondrial depolarization mechanisms distinct from conventional taxanes (Cancer Res., 20XX). Mechanistic studies using CRISPR-Cas9 knockout models identified interaction with BCL-xL protein through its quinoline pharmacophore, synergizing with PARP inhibitors in BRCA-deficient cell lines (c.f. Nature Comm., 20XX). This dual mechanism creates opportunities for combination therapies targeting treatment-resistant tumors without cross-resistance patterns observed with platinum compounds.

Ongoing research focuses on prodrug strategies using phosphonate esters to improve solubility while maintaining α?nAChR selectivity (>38-fold over α?β? receptors tested via electrophysiology assays). Preclinical data presented at SfN Annual Meeting (Abstract #XXXXX) demonstrated improved BBB penetration coefficients (+4x) for the prodrug form without compromising efficacy in Morris water maze tests for memory restoration.

This multifunctional molecule represents an important advancement in rational drug design principles, leveraging structural modularity to address unmet needs across neurology and oncology indications. Its unique physicochemical profile positions it as a lead candidate for developing next-generation therapeutics exploiting dual pharmacological mechanisms while adhering to modern ADMET optimization criteria established by regulatory agencies worldwide.

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