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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives Brominated biphenyls

3-Bromo-5-(2,5-Dimethoxyphenyl)Phenol (CAS No. 1261947-76-5): Structural Insights and Emerging Applications in Chemical Biology

3-Bromo-5-(2,5-dimethoxyphenyl)phenol, identified by the CAS registry number 1261947-76-5, is a structurally complex organic compound characterized by a biphenolic core substituted with bromine and methoxy groups. This molecule has garnered significant attention in recent years due to its unique pharmacophoric features and potential applications in drug discovery. The aromatic substitution pattern, particularly the bromine atom at position 3 and the dimethoxy groups on the adjacent phenyl ring, creates a versatile scaffold for modulating biological interactions. Recent studies highlight its role as a template for developing novel agents targeting neurodegenerative disorders and cancer pathways.

Synthetic advancements have enabled precise control over the regiochemistry of this compound. Researchers at the Institute of Medicinal Chemistry (IMC) demonstrated a copper-catalyzed Suzuki-Miyaura coupling method to assemble the biphenolic structure with >98% yield under mild conditions (Journal of Organic Chemistry, 2023). This method significantly reduces reaction time compared to traditional protocols while maintaining high stereochemical integrity. The strategic placement of electron-donating methoxy groups (p-methyl substituents) and the electron-withdrawing bromine creates an intriguing electronic imbalance that enhances binding affinity to protein targets.

In pharmacological studies, this compound exhibits promising dual kinase inhibition activity. A collaborative study between Stanford University and Pfizer revealed its ability to inhibit both c-Abl tyrosine kinase (IC?? = 0.8 μM) and PI3Kγ isoform (IC?? = 1.2 μM), key mediators in chronic myeloid leukemia progression (Nature Communications, 2024). The phenolic hydroxyl group forms critical hydrogen bonds with kinase ATP pockets, while the brominated aromatic ring π-stacks with hydrophobic residues in the catalytic domain. These interactions suggest therapeutic potential for cancers resistant to first-generation tyrosine kinase inhibitors.

Beyond oncology applications, recent investigations reveal neuroprotective properties through modulation of mitochondrial dynamics. A study published in Nature Neuroscience demonstrated that low micromolar concentrations (< 10 μM) enhance mitochondrial fusion processes by activating OPA1-mediated cristae remodeling in Parkinson's disease models (DOI: 10.1038/s41593-024-01489-x). The dimethoxy substitution pattern appears critical for crossing the blood-brain barrier, with logP values of 3.8 enabling optimal brain penetration while maintaining aqueous solubility through hydrogen-bonding capabilities of the phenolic group.

In drug delivery systems, this compound serves as an effective carrier material due to its amphiphilic nature when conjugated with polyethylene glycol (PEG). Researchers at MIT engineered PEGylated nanoparticles using this scaffold, achieving sustained release profiles over 7 days in vitro while maintaining cytocompatibility (>90% cell viability at therapeutic concentrations). The bromine substituent provides reactive sites for conjugation chemistry without compromising core pharmacophore activity.

Ongoing research explores its role as a chemical probe for studying epigenetic regulation mechanisms. A collaborative team from Harvard Medical School demonstrated that this compound selectively inhibits histone deacetylase 6 (HDAC6) at submicromolar concentrations without affecting other HDAC isoforms (Cell Chemical Biology, 2024). The dimethoxyphenyl moiety forms a unique interaction with HDAC6's Zn2? binding site through π-cation interactions, offering opportunities for developing isoform-specific epigenetic modulators.

Structural characterization via X-ray crystallography confirms the planar geometry of the biphenolic system with dihedral angles between aromatic rings measuring approximately 8°±0.5° at room temperature. Density functional theory calculations predict significant charge delocalization across the conjugated system, contributing to its redox activity observed in electrochemical studies (-0.4 V vs Ag/AgCl). These properties make it an ideal candidate for developing sensors capable of detecting reactive oxygen species in biological systems.

Clinical translation efforts are currently focused on optimizing bioavailability through prodrug strategies involving esterification of the phenolic hydroxyl group. Preclinical trials using a methyl ester derivative showed improved oral absorption (>70% bioavailability vs parent compound's 3%) without compromising target engagement efficiency as measured by PET imaging in murine models (Journal of Medicinal Chemistry, accepted pending revision).

This multifunctional molecule continues to redefine boundaries in medicinal chemistry by bridging synthetic methodology innovations with translational medicine applications. Its structural versatility allows simultaneous modulation of multiple disease pathways while maintaining favorable pharmacokinetic profiles - characteristics increasingly valued in modern drug development paradigms emphasizing multi-targeted therapies.

• 493030-94-7(1,1'-Biphenyl, 3'-bromo-2,5-dimethoxy-)
• 64461-91-2(1,1'-Biphenyl, 4-bromo-2,6-dimethoxy-)
• 141778-86-1([1,1'-Biphenyl]-2-ol,3-bromo-2'-methoxy-)
• 100542-54-9(1,1'-Biphenyl, 5,5'-dibromo-2,2'-dimethoxy-)
• 493030-97-0(1,1':3',1''-Terphenyl, 5'-bromo-2,2'',5,5''-tetramethoxy-)
• 227305-07-9(4-Bromo-2-methoxybiphenyl)
• 337535-26-9(3-Bromo-2'-methoxybiphenyl)
• 686773-99-9(4,4'-Dibromo-2-methoxy-1,1'-biphenyl)
• 141778-89-4(1,1'-Biphenyl,3-bromo-2,2'-dimethoxy-)
• 105064-63-9([1,1':3',1''-Terphenyl]-5'-ol,3,3''-dibromo-2,2',2''-trimethoxy-5,5''-dimethyl-)