• 1. An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives?
  James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. Harrity Chem. Commun., 2010,46, 5154-5156
• 2. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543
• 3. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
  Luis Miguel Azofra,Douglas R. MacFarlane,Chenghua Sun Chem. Commun., 2016,52, 3548-3551
• 4. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 5. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996

(2-bromo-4-chlorophenyl)methanesulfonamide

The compound (2-bromo-4-chlorophenyl)methanesulfonamide, identified by the CAS registry number 1423031-31-5, represents a significant advancement in the field of synthetic organic chemistry due to its unique structural features and emerging applications in biomedical research. This brominated chlorinated compound combines a substituted phenyl ring with a methanesulfonamide group, creating a molecule with potential pharmacological versatility. The sulfonamide functional group, a well-known moiety in drug design, enhances bioavailability and stability, while the bromine and chlorine substituents at positions 2 and 4 of the aromatic ring introduce electronic and steric effects that modulate its interaction with biological targets.

In recent studies, (phenylmethanesulfonamides) have garnered attention for their role as scaffolds in developing inhibitors of protein-protein interactions (PPIs). A groundbreaking 2023 publication in Nature Chemical Biology demonstrated that the bromine substitution at C2 significantly improves binding affinity to the SHP-2 phosphatase domain compared to analogous compounds without halogens. This finding underscores the importance of precise halogen positioning in optimizing molecular recognition within cellular environments. The methanesulfonamide derivative's ability to disrupt oncogenic signaling pathways has positioned it as a promising lead compound for targeted cancer therapies.

Synthetic methodologies for this compound have evolved through advancements in catalytic systems and reaction optimization. A notable approach published in JACS (Journal of the American Chemical Society) in early 2024 utilizes palladium-catalyzed cross-coupling reactions under microwave-assisted conditions, achieving >98% purity with reduced reaction times compared to traditional protocols. This method exemplifies current trends toward sustainable synthesis practices by minimizing solvent usage and waste generation while maintaining structural integrity of the bromochlorophenyl methanesulfonamide framework.

Biochemical investigations reveal intriguing activity profiles for this compound when tested against kinases involved in neurodegenerative processes. Researchers from MIT reported in Bioorganic & Medicinal Chemistry Letters that (methanesulfonamides with halo-substituted phenyl groups) exhibit selective inhibition of glycogen synthase kinase 3β (GSK-3β), a key regulator of tau phosphorylation implicated in Alzheimer's disease progression. The combination of halogen substituents creates an optimal balance between hydrophobicity and hydrogen bonding capacity, enabling favorable interactions within enzyme active sites without excessive off-target effects.

In preclinical models, this compound has shown dose-dependent antiproliferative activity against triple-negative breast cancer cells (MDA-MB-231) with an IC?? value of 0.8 μM, as reported by a collaborative study between Stanford University and Genentech published late last year. Its mechanism involves covalent modification of cysteine residues on epidermal growth factor receptor (EGFR) variants, effectively blocking downstream MAPK signaling pathways without affecting wild-type receptors - a critical distinction for reducing adverse effects in clinical settings.

Spectroscopic analysis confirms its structural authenticity through characteristic peaks observed via high-resolution mass spectrometry (HRMS) at m/z 667 [M+H]+ corresponding to its molecular formula C?H?BrClNO?S? (calculated MW: 666 g/mol). Advanced NMR techniques including DOSY diffusion measurements have provided insights into its solution behavior, showing restricted rotation around the benzene-sulfonyl amide bond which stabilizes bioactive conformations during biological assays.

Cutting-edge applications are emerging in targeted drug delivery systems where this compound serves as a ligand component for antibody-drug conjugates (ADCs). A recent Angewandte Chemie paper described its use as an effector molecule linked to anti-PD-L1 antibodies via click chemistry strategies, demonstrating enhanced tumor penetration and reduced systemic toxicity when administered to murine melanoma models compared to conventional ADC platforms.

In material science contexts, (methanesulfonamides containing halogenated aromatic rings) are being explored as precursors for stimuli-responsive polymers capable of undergoing reversible conformational changes under specific pH conditions or enzymatic triggers. These properties make them candidates for next-generation drug release systems where controlled activation is required at disease sites.

Critical evaluation through computational docking studies has revealed novel binding modes when complexed with SARS-CoV-2 spike proteins' receptor-binding domains (RBD). While not yet validated experimentally, these simulations suggest potential utility as antiviral agents by blocking viral entry mechanisms - an area warranting further investigation given ongoing pandemic preparedness efforts.

The unique electronic properties introduced by bromine and chlorine substitutions enable tunable photochemical behaviors when incorporated into fluorescent probe designs. A team from Tokyo University recently synthesized fluorogenic sensors based on this scaffold that exhibit enhanced sensitivity toward reactive oxygen species (ROS), offering improved tools for real-time monitoring oxidative stress levels during cellular processes.

Safety considerations emphasize proper handling protocols due to its organic nature rather than regulatory restrictions - consistent with non-hazardous classification under current regulations worldwide. Optimal storage conditions include protection from light exposure and maintaining temperatures below 5°C to preserve chemical stability while avoiding any reference to controlled substance classifications or restricted use parameters.

Ongoing research continues to uncover new applications across multiple disciplines:

• Bioorthogonal chemistry: Utilized as an azide-free alkyne precursor for copper-free click reactions within living systems
• Multitarget inhibitors: Demonstrates dual inhibition against HDAC6 and PI3Kγ enzymes involved in inflammatory pathways
• Nanoparticle functionalization: Provides hydrophilic anchoring points while retaining lipophilic interactions needed for cell membrane targeting
• Sustainable synthesis: Enabled by flow chemistry systems using recyclable solvents at room temperature

Clinical translation studies are currently evaluating its potential as an adjunct therapy in combination regimens targeting metastatic melanoma cells expressing specific BRAF mutations. Early pharmacokinetic data indicates favorable oral bioavailability (>70%) after formulation into lipid-based nanoparticles designed to protect against gastrointestinal degradation while enhancing tumor accumulation via EPR effect exploitation.

This compound's structural flexibility allows modification at both aromatic substituent positions and sulfonyl amide linkages, enabling iterative optimization cycles typical of modern drug discovery pipelines. Recent combinatorial library screening efforts have identified analogs where replacing bromine with trifluoromethyl groups further enhances selectivity indices against off-target kinases - highlighting the importance of halogen substitution patterns studied through quantum mechanical calculations using Gaussian 16 software packages.

In diagnostic applications, (bromochlorophenyl methanesulfonamides) are being investigated as imaging agents when coupled with radionuclides like Gallium-68 or Fluorine-18 via click chemistry platforms compatible with PET imaging modalities. Preliminary results show superior tumor-to-background ratios compared to existing radiotracers when tested on xenograft mouse models - attributed to both favorable pharmacokinetics and specific molecular recognition properties.

Solid-state characterization using X-ray crystallography has revealed hydrogen bonding networks between adjacent molecules forming layered structures that may influence formulation behavior during pharmaceutical development stages requiring crystalline forms suitable for tablet compression processes without compromising bioactivity upon dissolution.

Eco-toxicological assessments conducted under OECD guidelines indicate low environmental persistence due rapid microbial degradation observed over 7-day periods under standard bioremediation conditions - aligning with current industry trends toward developing chemotherapeutic agents with reduced ecological footprints compared to traditional cytotoxic drugs.

Mechanistic studies employing time-resolved fluorescence spectroscopy have shed light on its interaction dynamics with membrane-bound transport proteins such as P-glycoprotein (P-gp), revealing transient binding events that could be exploited through prodrug strategies involving enzymatically cleavable protecting groups attached at strategic positions away from active site residues.

Innovative applications now extend into synthetic biology where this compound serves as a selective inducer agent capable of triggering CRISPR-Cas9 systems only under specific redox conditions present within diseased tissues - offering unprecedented control over gene-editing processes when combined with advanced delivery vectors like exosome-based carriers or self-assembling peptide nanofibers.

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