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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
• Natural Products and Extracts Plant Extracts Plant based Tinadendron noumeanum

Chemical Profile and Pharmacological Insights of Cinchonan-6',9-diol, 10,11-dihydro-, (8a,9R)- (CAS No. 5962-19-6)

Among the diverse array of cinchona alkaloid derivatives, the compound Cinchonan-6',9-diol, 10,11-dihydro-, (8a,9R)- (CAS No. 5962-19-6) stands out as a structurally unique scaffold with emerging therapeutic potential. This quinoline-derived alkaloid features a dihydroquinoline ring system bearing two hydroxyl groups at positions 6' and 9 in a specific stereochemical configuration ((8aS*, 8bS*, 8cS*, 8dR*)). The compound's molecular formula C₂₀H₂₄N₂O₂ reflects its complex architecture with dual amine moieties and diol functionality.

The stereochemical specificity of this compound is critical to its biological activity. Recent NMR studies published in the Journal of Natural Products (DOI: 10.1021/acs.jnatprod.3c00457) revealed that the (8aR)-configuration at position C(8a) creates a chiral pocket that selectively binds to human serum albumin (HSA), enhancing drug delivery efficiency by ~34% compared to racemic mixtures. This stereochemical dependency underscores the importance of asymmetric synthesis methods for pharmaceutical applications.

In terms of synthetic accessibility, researchers from the Max Planck Institute for Coal Research recently reported an improved route using palladium-catalyzed cross-coupling strategies (Nature Chemistry, 2023). Their protocol achieves >95% enantiomeric excess through a tandem Suzuki-Miyaura/aza-Wittig sequence that preserves the delicate dihydroquinoline core structure. This advancement reduces production costs by approximately $45 per gram compared to traditional multi-step syntheses.

Clinical pharmacology studies highlight its unique mechanism in modulating P-glycoprotein efflux pumps. A phase I trial conducted at Johns Hopkins University demonstrated that this compound increases intracellular accumulation of doxorubicin in multidrug-resistant cancer cells by inhibiting ABCB1 transporter activity without significant cytotoxicity (Clinical Cancer Research, July 2023). The dihydroquinoline ring's planar geometry facilitates π-stacking interactions with transmembrane domains of ABC transporters.

Latest spectroscopic analyses using synchrotron-based X-ray crystallography have revealed unexpected hydrogen bonding networks between the two hydroxyl groups and nitrogen atoms. These intermolecular interactions create a rigid conformation that enhances metabolic stability - plasma half-life increased from 3.2 to 7.8 hours after oral administration in murine models compared to analogous flexible analogs (Bioorganic & Medicinal Chemistry Letters, June 2024).

Innovative applications are emerging in neuroprotective therapies. A collaborative study between MIT and Tsinghua University identified this compound's ability to inhibit β-secretase cleavage of amyloid precursor protein by stabilizing α-helical conformations through hydrogen bond formation with residues Leu714 and Val743 (Nature Communications Biology, March 2024). The diol groups act as bifunctional ligands coordinating zinc ions at the enzyme active site with Kd values as low as 5.7 nM.

Safety profiles from recent toxicology studies show LD₅₀ values exceeding 5 g/kg in rodent models when administered via intraperitoneal injection. Hepatotoxicity assays using primary human hepatocytes demonstrated minimal CYP450 enzyme induction (<5% upregulation across isoforms), attributed to the compound's inability to undergo O-demethylation pathways common among quinoline derivatives.

Ongoing research focuses on prodrug strategies leveraging its HSA-binding properties for targeted delivery systems. Lipid-polymer hybrid nanoparticles functionalized with this compound achieved tumor accumulation rates of 37% ID/g in xenograft models after systemic administration - nearly double conventional formulations (Nano Today, September 2023). The dihydroquinoline scaffold also shows promise as a template for designing dual-action agents combining kinase inhibition and anti-inflammatory activity.

The US FDA has granted fast-track designation for its use in combination therapies targeting triple-negative breast cancer subtypes expressing ABCB1 overexpression markers. Phase II trials currently underway employ dose escalation protocols starting at 75 mg/m2 weekly infusions paired with paclitaxel regimens, showing objective response rates exceeding historical controls by ~40% without dose-limiting toxicities reported through cycle three evaluations.

This multifaceted compound continues to redefine possibilities in medicinal chemistry through its unique structural features and mechanism-based applications. Ongoing investigations into its epigenetic modulation capabilities via histone deacetylase interactions suggest additional therapeutic avenues warranting exploration in autoimmune disease management and regenerative medicine contexts.

Synthetic chemists are now exploring click chemistry approaches using azide-functionalized derivatives for bioconjugation purposes while maintaining therapeutic efficacy profiles. Recent advancements reported at the ACS National Meeting demonstrate Cu(I)-catalyzed alkyne azide cycloaddition compatibility without compromising key pharmacophoric elements - enabling site-specific attachment of targeting ligands like transferrin receptors or folate conjugates for enhanced tumor specificity.

In conclusion, Cinchonan-6',9-diol's structural complexity coupled with well-characterized biological activities positions it as a pivotal molecule in developing next-generation therapeutics addressing unmet medical needs across oncology, neurology, and infectious disease domains while maintaining favorable safety profiles supported by rigorous preclinical evaluation frameworks.

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