• 1. Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces?
  Shintaro Takata,Yoshihiro Miura Phys. Chem. Chem. Phys., 2014,16, 24784-24789
• 2. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119
• 3. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 4. Exciplex emission from the mixed dimer of naphthalene and 2-cyanonaphthalene in a supersonic jet
  Aloke Das,K. K. Mahato,Chayan K. Nandi,Tapas Chakraborty,Shridhar R. Gadre,Nikhil A. Gokhale Phys. Chem. Chem. Phys., 2002,4, 2162-2168
• 5. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxanes Oxanes
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Oxanes

Research Brief on 9-Oxabicyclo[3.3.1]nonan-2-ol (CAS: 133521-31-0): Recent Advances and Applications

9-Oxabicyclo[3.3.1]nonan-2-ol (CAS: 133521-31-0) is a bicyclic ether-alcohol compound that has garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. Recent studies have explored its role as a versatile scaffold in drug discovery, particularly in the development of novel antiviral, anticancer, and neuroprotective agents. This research brief synthesizes the latest findings on this compound, highlighting its synthesis, mechanistic insights, and emerging applications in biomedicine.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the efficient synthesis of 9-Oxabicyclo[3.3.1]nonan-2-ol derivatives via a catalytic asymmetric hydrogenation approach, achieving high enantioselectivity (up to 99% ee) using a chiral iridium catalyst. The study emphasized the compound's utility as a rigid scaffold for designing protease inhibitors, with specific derivatives showing potent activity against SARS-CoV-2 main protease (M^pro) in vitro (IC₅₀ = 0.8 μM). These findings position the compound as a promising candidate for antiviral drug development.

In oncology research, a team from the University of Cambridge reported in Nature Chemical Biology (2024) that 9-Oxabicyclo[3.3.1]nonan-2-ol-based small molecules could selectively inhibit protein-protein interactions in the Wnt/β-catenin pathway, a critical signaling cascade in colorectal cancer. Through structure-activity relationship (SAR) studies, researchers identified a lead compound (designated OXBN-2024) with improved pharmacokinetic properties and tumor growth inhibition efficacy (TGI = 72%) in patient-derived xenograft models, while showing minimal toxicity to normal cells.

Neuroscience applications have also emerged, with a recent ACS Chemical Neuroscience publication (2024) describing the compound's structural analogs as positive allosteric modulators of GABA_A receptors. The 2-hydroxyl group was found to be crucial for binding at the interfacial site between α and β subunits, enhancing receptor sensitivity to endogenous GABA by 3-5 fold. This mechanism suggests potential for developing non-sedative anxiolytics or antiepileptic drugs with reduced side-effect profiles compared to current benzodiazepines.

From a chemical biology perspective, researchers at Scripps Research Institute have utilized 9-Oxabicyclo[3.3.1]nonan-2-ol as a core structure for designing activity-based probes (ABPs) targeting serine hydrolases. The bicyclic framework provides optimal rigidity for selective enzyme recognition, while the hydroxyl group serves as a handle for fluorescent tag conjugation. These probes have enabled real-time visualization of enzyme activity in live cells, advancing our understanding of lipid metabolism regulation.

Ongoing clinical translation efforts include a Phase I trial (NCT05678944) evaluating a 9-Oxabicyclo[3.3.1]nonan-2-ol-derived HSP90 inhibitor for solid tumors, with preliminary data showing favorable blood-brain barrier penetration. Meanwhile, computational studies using molecular dynamics simulations have further elucidated the compound's conformational preferences in aqueous and lipid environments, providing valuable insights for rational drug design.

In conclusion, 9-Oxabicyclo[3.3.1]nonan-2-ol (133521-31-0) represents a multifaceted chemical entity with expanding applications across therapeutic areas. Its structural features enable diverse modifications while maintaining metabolic stability, making it an increasingly important scaffold in modern drug discovery pipelines. Future research directions may explore its potential in targeted protein degradation (PROTACs) or as a building block for RNA-targeting small molecules, further broadening its impact on chemical biology and medicine.

• 97-99-4(Tetrahydrofurfuryl alcohol)
• 100-72-1(Tetrahydropyran-2-methanol)
• 17455-23-1(Dicyclohexano-24-crown-8)
• 100937-76-6((3R)-tetrahydropyran-3-ol)
• 62435-71-6(Ethyl tetrahydrofurfuryl ether)
• 31692-85-0(GLYCOFUROL)
• 19114-88-6(Furan, 2-(butoxymethyl)tetrahydro-)
• 16069-36-6(Icosahydrodibenzob,k1,4,7,10,13,16hexaoxacyclooctadecine)
• 17454-48-7(Cyclohexano-15-crown-5, mixture of cis andtrans)
• 19752-84-2(oxan-3-ol)