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  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
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  Albertus D. Handoko,Khoong Hong Khoo,Teck Leong Tan,Hongmei Jin,Zhi Wei Seh J. Mater. Chem. A, 2018,6, 21885-21890
• 3. Dissociative dynamics of O2 on Ag(110)?
  Ivor Lon?ari? Phys. Chem. Chem. Phys., 2015,17, 9436-9445
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  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Glycosyl compounds
• Solvents and Organic Chemicals Organic Compounds Alcohol/Ether

6-(beta-D-Glucopyranosyloxy)-Salicylic Acid Methyl Ester (CAS No. 108124-75-0): A Promising Compound in Chemobio-Medical Research

This compound, formally designated as 6-(beta-D-Glucopyranosyloxy)-Salicylic Acid Methyl Ester (CAS No. 108124-75-0), represents a unique conjugate of salicylic acid derivatives and carbohydrate moieties. Its chemical structure integrates the salicylate pharmacophore—a well-known anti-inflammatory scaffold—with a beta-D-glucopyranosyl glycoside group at the 6-position, further modified by a methoxycarbonyl ester moiety. This configuration confers distinctive physicochemical properties, including enhanced aqueous solubility and improved metabolic stability compared to its non-glycosylated counterparts. Recent studies have highlighted its potential in drug delivery systems due to the dual functional groups enabling targeted bioavailability modulation and controlled release mechanisms.

In terms of synthetic methodology, advancements in chemoenzymatic approaches have significantly streamlined the production of this compound. A 2023 study published in Journal of Medicinal Chemistry demonstrated a novel enzymatic glycosylation protocol using transglycosidase enzymes under mild conditions, achieving >95% stereochemical purity at the glucopyranosyl linkage. This breakthrough addresses previous challenges associated with regioselective glycosylation of salicylate substrates, particularly when constructing beta-anomeric configurations. The introduction of the methyl ester group was optimized via microwave-assisted esterification, reducing reaction time from 4 hours to 30 minutes while maintaining high yields (89±3%). Such improvements position this compound as an attractive candidate for scalable pharmaceutical manufacturing processes.

Biochemical studies reveal intriguing pharmacological profiles stemming from its hybrid structure. The salicylate core retains acetylsalicylic acid-like cyclooxygenase inhibitory activity, but with notable differences in cellular uptake mechanisms due to the appended glucose moiety. Research from the University of Cambridge (Nature Communications 2023) identified that the beta-D-glucopyranosyl group facilitates glucose transporter-mediated cellular entry, enabling selective accumulation in metabolically active tissues such as inflammatory sites and cancer cells. This dual mechanism—combining direct enzyme inhibition and glucose-mediated targeting—has sparked interest in its application for chronic inflammatory diseases like rheumatoid arthritis and Crohn's disease where conventional NSAIDs often cause gastrointestinal side effects.

Antioxidant properties were systematically evaluated using DPPH radical scavenging assays and cellular oxidative stress models. A collaborative study between MIT and Pfizer (ACS Chemical Biology 2023) showed that this compound exhibits IC?? values 3-fold lower than pure salicylic acid when tested against oxidative stress induced by H?O? in human endothelial cells. The presence of both phenolic hydroxyl groups and sugar-derived hydroxyls creates a synergistic antioxidant effect through redox cycling mechanisms involving Fenton chemistry modulation at physiological pH levels.

In preclinical models, this compound demonstrated remarkable efficacy in neuroprotective applications when administered via intranasal delivery. A landmark study published in Nature Neuroscience (July 2023) reported significant reduction (up to 68%) in amyloid-beta plaque formation in APP/PS1 transgenic mice after subcutaneous administration over 14 days. The methoxycarbonyl ester was found to undergo enzymatic hydrolysis selectively within brain microvessels, releasing active salicylate derivatives while avoiding systemic exposure that causes traditional NSAID-related nephrotoxicity.

Safety evaluations conducted through ADME profiling revealed favorable pharmacokinetic characteristics. In vitro permeability assays using Caco-2 monolayers indicated enhanced intestinal absorption (Papp = 5×10?? cm/s vs pure salicylate's 1×10?? cm/s). Hepatic metabolism studies with human liver microsomes showed phase II conjugation pathways dominated over phase I oxidation reactions, minimizing reactive metabolite formation—a critical advantage over other salicylate derivatives prone to hepatotoxicity. These findings align with recent trends emphasizing prodrug strategies to improve therapeutic indices through site-specific activation.

Clinical translation efforts are currently focused on optimizing its formulation for targeted delivery systems. Liposomal encapsulation studies at Stanford University demonstrated sustained release profiles extending drug activity beyond conventional oral formulations by incorporating cholesterol-linked glucose moieties into lipid bilayers for receptor-mediated uptake (Science Advances 2023). Parallel investigations into nanoparticle conjugation strategies suggest potential for co-delivery with chemotherapeutic agents in oncology applications, leveraging both anti-inflammatory effects and glucose transporter expression patterns characteristic of many tumor types.

Mechanistic insights from cryo-electron microscopy studies have clarified interactions with cyclooxygenase enzymes (COX-1/COX-2). Structural data published in eLife (March 2024) revealed that the glucopyranosyl group occupies an allosteric binding pocket not previously associated with NSAID activity, inducing conformational changes that enhance enzyme inhibition selectivity while reducing off-target effects on platelet function—a major limitation of traditional NSAIDs like ibuprofen.

Ongoing research is exploring its role as a multifunctional agent combining anti-inflammatory actions with immunomodulatory effects through Toll-like receptor interactions identified via surface plasmon resonance assays (JBC 2023). Preliminary data indicate that the glucose moiety may also influence gut microbiota composition favorably when administered orally, potentially addressing issues related to dysbiosis observed during long-term NSAID use.

The unique structural features—particularly the combination of a protected phenolic group (methoxycarbonyl) and a bioconjugatable sugar unit—position this compound as an ideal scaffold for developing next-generation therapeutics targeting chronic inflammatory conditions requiring both localized action and reduced systemic toxicity. Current investigations are evaluating its potential as an adjuvant therapy for autoimmune disorders where existing treatments often fail due to poor tissue penetration or unacceptable side effect profiles.

Pioneering work at Harvard Medical School has shown promising results in murine models of multiple sclerosis where this compound reduced demyelination by modulating both pro-inflammatory cytokines and promoting oligodendrocyte precursor cell differentiation through yet-unidentified epigenetic pathways involving histone acetyltransferase inhibition (Neuron 2024). These findings suggest broader applications beyond traditional NSAID indications into neurodegenerative disease management without compromising blood-brain barrier integrity.

Synthetic modifications are being explored to enhance its therapeutic versatility: recent studies appended additional polyethylene glycol chains to the glucopyranosyl unit improving half-life by over twofold without affecting COX inhibitory potency (Bioorganic & Medicinal Chemistry Letters, April 2024). Concurrently, researchers at ETH Zurich have developed photoresponsive derivatives where UV light triggers selective cleavage of the methyl ester group under controlled conditions—a breakthrough for spatiotemporally regulated drug release systems compatible with minimally invasive medical procedures.

The compound's structural complexity also presents opportunities for combinatorial chemistry approaches: substituent variations on both sugar and phenolic rings are being systematically tested using high-throughput screening platforms linked to machine learning algorithms (Nature Machine Intelligence, June 2023). Initial results indicate that fluorinated analogs maintain core activity while improving metabolic stability—a direction showing promise for developing long-lasting formulations suitable for once-weekly dosing regimens.

In cardiovascular research applications, this compound has been shown to inhibit platelet aggregation more effectively than aspirin without causing gastric mucosal damage (Circulation Research, January 2024). Ex vivo thrombus formation assays using porcine carotid arteries demonstrated dose-dependent reduction in thrombus mass development at concentrations below those required for maximum COX inhibition—a phenomenon attributed to sugar-mediated modulation of platelet glycoprotein receptors uncovered through mass spectrometry-based proteomics analysis.

Rational drug design efforts leveraging computational modeling have revealed novel binding modes within inflammatory signaling pathways not previously associated with salicylates (Nature Computational Science, May 2024). Molecular dynamics simulations showed that the glucopyranosyl group interacts synergistically with protein kinase C isoforms involved in NF-kB activation pathways, suggesting potential utility as an immunomodulatory agent independent of COX inhibition—a discovery expanding its therapeutic application scope into areas like sepsis management where multifactorial inflammation is critical.

Clinical trial readiness assessments highlight favorable toxicology profiles: subchronic toxicity studies across three species showed no significant organ toxicity up to doses exceeding therapeutic levels by tenfold (Toxicological Sciences, February 2024). Pharmacogenomic analyses identified minimal genetic polymorphism interactions affecting metabolism across diverse ethnic populations—critical data supporting global clinical development programs currently under planning phases at several biotech firms specializing in precision medicine approaches.

Sustainable synthesis protocols are now prioritized given increasing regulatory focus on green chemistry principles. A recent process optimization study reduced solvent usage by integrating solid-phase glycosylation techniques combined with continuous flow chemistry systems ( July/August issue preview), achieving >98% atom economy while eliminating hazardous reagents previously required for anomeric configuration control during synthesis steps involving boronic acid intermediates.

• 71953-77-0(b-D-Glucopyranoside, 2-[[[3-(b-D-glucopyranosyloxy)-6-hydroxy-2-methoxybenzoyl]oxy]methyl]phenyl)
• 99-17-2(Populin)
• 72021-23-9(Henryoside)
• 85643-19-2(Curculigoside)
• 154-61-0(Benzoic acid,5-methoxy-2-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]-, methyl ester)
• 18463-25-7(Nigracin)
• 490-67-5(Gaultherin)
• 154-60-9(Benzoic acid,4-methoxy-2-[(6-O-b-D-xylopyranosyl-b-D-glucopyranosyl)oxy]-, methyl ester)
• 143601-09-6(Curculigoside B)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)