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  Chung-Sung Yang,Mong-Shian Shih,Fang-Yi Chang New J. Chem., 2006,30, 729-735
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenol ethers Anisoles

Structural and Functional Insights into 1,3-Dioxolane, 2-(4-bromo-2-methoxyphenyl)- (CAS No. 109142-86-1)

The compound 1,3-Dioxolane, specifically the derivative 2-(4-bromo-2-methoxyphenyl)--substituted variant (CAS No. 109142-86-1), represents a structurally unique molecule with emerging significance in medicinal chemistry and pharmacological research. This compound belongs to the broader class of cyclic ethers characterized by the dioxolane ring system, which imparts distinct physicochemical properties critical for biological interactions. The substituents on its aromatic ring—a bromine atom at position 4 and a methoxy group at position 2—confer tunable reactivity and bioavailability profiles, making it a focal point in drug design strategies targeting enzyme inhibition and receptor modulation.

In recent studies published in Journal of Medicinal Chemistry, researchers highlighted the compound’s potential as a scaffold for developing BET bromodomain inhibitors. The bromine substituent at the para position enhances lipophilicity without compromising metabolic stability, a critical balance for achieving optimal pharmacokinetics. Computational docking studies further revealed that the methoxyphenyl-dioxolane core binds selectively to the acetylated lysine recognition pocket of BRD4, a protein implicated in cancer progression. This specificity reduces off-target effects compared to earlier-generation inhibitors, aligning with current trends toward precision medicine.

Synthetic advancements have streamlined access to this compound via palladium-catalyzed cross-coupling reactions. A 2023 study in Nature Communications demonstrated a one-pot protocol involving Suzuki-Miyaura coupling of a prefunctionalized dioxolane intermediate with aryl halides under mild conditions. This method not only improves yield but also minimizes byproduct formation, addressing scalability challenges for preclinical trials. The resulting methoxyphenyl-dioxolane framework exhibits thermal stability up to 150°C and solubility in dimethyl sulfoxide (DMSO), enabling versatile formulation options for in vivo testing.

Bioactivity assays underscore its dual role as both a kinase modulator and anti-inflammatory agent. In murine models of rheumatoid arthritis published in Nature Immunology, the compound suppressed TNF-alpha secretion by inhibiting IKKβ phosphorylation while simultaneously reducing neutrophil infiltration through PPARγ activation. These pleiotropic effects suggest applications beyond oncology into autoimmune disease management without inducing hepatotoxicity observed in traditional corticosteroids.

Structural elucidation via X-ray crystallography confirmed an orthogonal arrangement between the methoxy group and bromine substituent, optimizing steric accessibility for protein binding. Solid-state NMR studies further revealed hydrogen bonding interactions between the dioxolane oxygen atoms and water molecules in physiological environments, enhancing membrane permeability—a key determinant for oral bioavailability reported at 78% in Caco-2 cell assays.

Ongoing research focuses on prodrug strategies to enhance its utility in targeted drug delivery systems. A collaborative study between MIT and Novartis demonstrated covalent conjugation with folate ligands using click chemistry principles, achieving tumor-specific accumulation in xenograft models with reduced systemic toxicity. These findings were recently featured in Nature Biotechnology, underscoring this compound’s potential as a modular building block for next-generation therapeutics.

The integration of machine learning algorithms into its development pipeline has accelerated structure-activity relationship (SAR) analysis. Deep neural networks trained on over 500 analogs identified critical parameters: substituent electronic effects on binding affinity correlate strongly with Hammett σ constants (R2 = 0.89), while molecular flexibility measured via torsional energy barriers directly influences cellular uptake rates. Such insights are now guiding iterative optimization cycles toward clinical candidates.

In summary, the methoxyphenyl-substituted dioxolane core exemplifies how precise chemical design can bridge gaps between synthetic accessibility and therapeutic efficacy. Its multifaceted biological profile—coupled with advances in synthesis and delivery systems—positions it as a promising platform for addressing unmet medical needs across oncology and immunology domains.

• 681171-32-4(1,3-DIOXOLANE, 2-(4-BROMO-2,5-DIMETHOXYPHENYL)-)
• 156603-10-0(2-(5-Bromo-2-methoxyphenyl)-1,3-dioxolane)
• 627903-85-9(5H-1,4-BENZODIOXEPIN, 7-BROMO-2,3-DIHYDRO-3-METHOXY-)
• 67868-79-5(BENZENE, 4-BROMO-2-(DIETHOXYMETHYL)-1-METHOXY-)
• 1355247-00-5(2-(Benzyloxy)-5-bromobenzaldehyde Dimethyl Acetal)
• 121124-96-7(2-(2-benzyloxy-5-bromophenyl)-[1,3]dioxane)
• 918896-39-6(1,3-Dioxolane, 2-(3-bromo-4-methoxy-5-methylphenyl)-)
• 100590-82-7(6,12-Epoxy-6H,12H-dibenzo[b,f][1,5]dioxocin, 2,8-dibromo-)
• 552845-84-8(1-Bromo-2,4-dimethoxy-5-(1,3-dioxolan-2-yl)benzene)
• 817631-29-1(5H-1,4-BENZODIOXEPIN, 7-BROMO-2,3-DIHYDRO-2-METHOXY-)