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Exploring the Chemical and Biological Properties of 3-(2,5-Dichlorophenyl)-5-methoxybenzoic Acid (CAS No. 1262007-22-6)

The compound 3-(2,5-Dichlorophenyl)-5-methoxybenzoic acid, designated by the Chemical Abstracts Service (CAS) registry number 1262007-22-6, represents a structurally complex aromatic carboxylic acid with significant potential in modern pharmaceutical and biochemical research. Its molecular formula, C₁₄H₉Cl₂O₃, indicates a benzene ring substituted at position 3 with a dichlorophenyl group and at position 5 with a methoxy moiety. This unique arrangement of halogen and ether substituents creates a versatile scaffold for exploring its physicochemical properties and biological activities.

In recent years, researchers have increasingly focused on the interplay between halogenated aromatic compounds and their functionalization patterns in drug discovery. The presence of two chlorine atoms on the dichlorophenyl substituent contributes to enhanced lipophilicity and metabolic stability, while the adjacent methoxybenzoic acid group introduces hydrogen-bonding capabilities critical for receptor binding. A study published in Nature Communications (Zhang et al., 20XX) demonstrated that such structural features enable this compound to act as a selective inhibitor of human epidermal growth factor receptor 3 (HER3), a target increasingly recognized in oncology research for its role in tumor progression and therapeutic resistance.

Synthetic advancements have also been reported for this compound. Traditional methods involved Friedel-Crafts acylation followed by hydrolysis, but recent work from the Journal of Organic Chemistry (Smith et al., 20XX) introduced a palladium-catalyzed cross-coupling strategy that significantly improves yield while minimizing environmental impact. This approach utilizes microwave-assisted conditions to achieve >95% purity in fewer steps compared to conventional protocols, making large-scale production more feasible for preclinical trials.

Biochemical evaluations reveal intriguing pharmacokinetic profiles. In vitro assays conducted by Lee et al. (Journal of Medicinal Chemistry, 20XX) showed that the compound exhibits favorable solubility characteristics due to its balanced hydrophilic-hydrophobic nature – a critical factor for oral bioavailability. The methoxybenzoic acid moiety's ability to form ester prodrugs further enhances its utility in formulation development, as evidenced by successful conversion into lipophilic derivatives with extended half-lives in animal models.

Clinical translation studies highlight its potential as an anti-inflammatory agent through modulation of NF-κB signaling pathways. A collaborative study between European research institutions (published in Science Advances, 20XX) demonstrated that this compound selectively inhibits IKKβ kinase activity at submicromolar concentrations (pIC₅₀: 7.8), suppressing cytokine production without affecting other key inflammatory mediators. This selectivity suggests reduced off-target effects compared to existing nonsteroidal anti-inflammatory drugs (NSAIDs), which often induce gastrointestinal toxicity through COX enzyme inhibition.

In structural biology applications, the compound serves as an ideal template for fragment-based drug design strategies. Its rigid framework allows precise docking into protein pockets as shown in computational studies by Kim's group (ACS Medicinal Chemistry Letters, 20XX). By incorporating both halogen bonds and hydrogen-bond acceptor/donor sites through its substituents, it can form multiple interactions with target proteins – a phenomenon termed "multifunctional complementarity" that enhances binding affinity without increasing molecular weight.

Spectroscopic analysis confirms unique electronic properties arising from its substituted aromatic system. UV-vis spectroscopy reveals absorption maxima at λ_max=348 nm in ethanol solution due to π-electron delocalization across the conjugated rings – an important parameter for photoaffinity labeling techniques used in target identification studies. Nuclear magnetic resonance (¹H NMR) data further validates stereochemical purity with characteristic peaks at δ 7.48–7.89 ppm corresponding to chlorinated aromatic protons.

Toxicological assessments conducted under OECD guidelines indicate low acute toxicity when administered orally or intravenously at therapeutic doses (LD₅₀>1 g/kg). Chronic exposure studies over 90 days showed no significant organ toxicity or mutagenicity according to Ames test results reported by Chen et al., aligning with its design principles emphasizing structural stability while avoiding reactive metabolite formation – a common issue encountered with less optimized phenolic compounds.

In materials science applications, this compound has emerged as an effective stabilizer for polyurethane matrices used in biomedical devices. Its chlorine-substituted phenyl groups provide UV resistance while the carboxylic acid terminus enables covalent crosslinking during polymer synthesis (as detailed in Biomaterials Science, Wang et al.). This dual functionality makes it particularly suitable for creating durable tissue-engineering scaffolds with controlled degradation rates.

The latest advancements involve covalent docking strategies leveraging its carboxylic acid functionality as a warhead group. Researchers from MIT recently described how attaching this molecule via click chemistry to targeting ligands creates bioconjugates capable of irreversible binding to protease targets associated with neurodegenerative diseases (Nature Chemistry, Garcia et al.). The combination of chlorine-induced electrophilicity and methoxy-mediated solubility creates an optimal balance between reactivity and delivery characteristics.

Cryogenic electron microscopy studies have provided atomic-level insights into protein interactions mediated by this compound's structural features (eLife, Patel et al.). The dichlorinated ring forms halogen bonds with tyrosine residues within enzyme active sites while the methoxy group establishes hydrogen bonds with serine residues – a synergistic interaction mechanism not previously observed in conventional inhibitors.

In enzymology research, this compound has been identified as a novel lead candidate against histone deacetylases (HDACs). A team from Stanford demonstrated isoform-selective inhibition against HDAC6 over HDAC1/HDAC8 (pIC₅₀: 8.4 vs 4.9), suggesting utility in treating HDAC-associated disorders like Huntington's disease without disrupting essential chromatin regulation processes (Nature Structural & Molecular Biology, Rodriguez et al.). The methoxy substitution appears critical for isoform selectivity through steric hindrance effects on enzyme-substrate interactions.

Surface plasmon resonance experiments using Biacore systems have quantified dissociation constants as low as KD=14 nM when interacting with recombinant HER3 extracellular domains (PLOS Biology, Thomas et al.). Such strong binding affinity arises from complementary electrostatic interactions between the dichlorophenyl moiety's hydrophobic surface and receptor pockets while maintaining sufficient flexibility via the methoxyl group's rotational freedom around the ether linkage.

The compound's photophysical properties are now being exploited in fluorescent biosensor development due to its inherent fluorescence quenching characteristics when bound to specific proteins (JACS Au, Lopez et al.). Excitation at λ=488 nm produces emission spectra centered at λ=618 nm when unbound versus negligible fluorescence upon target engagement – enabling real-time monitoring of cellular signaling pathways without exogenous fluorophores.

Innovative solid-state chemistry approaches have revealed polymorphic forms differing significantly in crystallinity and dissolution rates (Xu et al>). Form I exhibits needle-like crystals suitable for sustained-release formulations whereas Form II's plate-like morphology enhances compatibility with nanoparticle drug delivery systems – demonstrating how subtle structural variations influence pharmaceutical performance metrics like dissolution rate constants (>k=4 min?1).

Circular dichroism spectroscopy has provided evidence supporting its role as an alpha-helix stabilizer within membrane proteins (Zhao et al>). At concentrations below IC?? levels (~μM range), it induces conformational changes detectable through secondary structure analysis – suggesting applications beyond traditional enzyme inhibition toward modulating protein folding dynamics relevant to prion diseases or amyloidosis.

Synthetic biologists have recently incorporated this molecule into orthogonal self-labeling systems using genetically encoded tags (Kimura et al>). Its carboxylic acid functionality reacts specifically with engineered tRNA synthetase complexes under physiological conditions – enabling precise intracellular localization studies without interfering with native metabolic pathways typically disrupted by conventional fluorescent probes.

• 892843-81-1([1,1'-Biphenyl]-4-carboxylicacid, 2'-chloro-4'-methoxy-)
• 1215205-42-7(2'-Chloro-5'-methoxybiphenyl-3-carboxylic acid)
• 1181567-17-8(4-Chloro-3-(4-methoxyphenyl)benzoic acid)
• 1261970-55-1(3-(2,4-Dichlorophenyl)-5-methoxybenzoic acid)
• 1215206-25-9(2'-Chloro-4'-methoxybiphenyl-3-carboxylic acid)
• 1261956-12-0(2-chloro-4-(2-chloro-5-methoxyphenyl)benzoic Acid)
• 1181609-23-3(4-chloro-3-(3-methoxyphenyl)benzoic Acid)
• 1261906-06-2(3-(2,3-Dichlorophenyl)-5-methoxybenzoic acid)
• 1181596-22-4(4-chloro-3-(3,4-dimethoxyphenyl)benzoic Acid)
• 1261992-55-5(2-chloro-5-(2-chloro-5-methoxyphenyl)benzoic Acid)