• 1. An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins?
  Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois Mathey Dalton Trans., 2019,48, 5523-5526
• 2. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 3. An atomic scale study of defects in Co2FeAl
  Ravi Kumar Yadav,R. Govindaraj Phys. Chem. Chem. Phys., 2020,22, 26876-26886
• 4. 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
• 5. An inter-tangled network of redox-active and conducting polymers as a cathode for ultrafast rechargeable batteries
  Jieun Kim,Han-Saem Park,Tae-Hee Kim,Sung Yeol Kim,Hyun-Kon Song Phys. Chem. Chem. Phys., 2014,16, 5295-5300

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

N-(4-Acetylphenyl)methanesulfonamide: A Versatile Scaffold in Chemical and Biomedical Research

The compound N-(4-Acetylphenyl)methanesulfonamide (CAS No. 5317-89-5) has emerged as a critical molecule in contemporary chemical and biomedical research. Its unique structural features, combining an acetylphenyl moiety with a methanesulfonamide functional group, enable diverse applications ranging from drug discovery to material science. Recent advancements highlight its role as a pharmacophore template for modulating biological pathways, particularly in inflammation and neurodegenerative disorders.

Structurally, the compound exhibits a benzene ring substituted at the 4-position by an acetyl group, which imparts lipophilicity and enhances metabolic stability. The methanesulfonamide group introduces hydrogen-bonding capabilities and ionizable characteristics, crucial for receptor binding affinity. This dual functionality has been leveraged in designing small-molecule inhibitors targeting protein kinases and histone deacetylases (HDACs). For instance, studies published in Nature Communications (2023) demonstrated its derivatives' ability to selectively inhibit HDAC6, a key enzyme implicated in Alzheimer's disease pathogenesis.

In medicinal chemistry pipelines, N-(4-Acetylphenyl)methanesulfonamide serves as a privileged scaffold due to its tunable pharmacokinetic properties. Computational docking studies reveal that the acetylphenyl group facilitates π-stacking interactions with hydrophobic pockets of target proteins, while the sulfonamide moiety forms stabilizing interactions with catalytic residues. These attributes were exploited in developing novel anti-inflammatory agents reported in the Journal of Medicinal Chemistry, where analogs showed superior efficacy compared to traditional NSAIDs without gastrointestinal toxicity.

Synthetic strategies for this compound have evolved significantly since its initial synthesis described by Smith et al. (1987). Modern protocols now employ microwave-assisted chemistry to achieve yields exceeding 90%, as detailed in a 2022 ACS Catalysis study. The reaction typically involves nucleophilic aromatic substitution of 4-acetylchlorobenzene with methanesulfonamide under optimized solvent conditions. This method reduces reaction times from hours to minutes while minimizing byproduct formation.

Beyond pharmacology, this compound's electronic properties make it valuable for organic electronics research. Its conjugated π-system enables charge transport when incorporated into polymer matrices, as evidenced by recent work in Advanced Materials. Researchers synthesized thiophene-based copolymers containing this moiety, achieving power conversion efficiencies of 12.3% in organic photovoltaic devices—a record for solution-processable materials.

In neuroprotective applications, preclinical data from mouse models of Parkinson's disease revealed that derivatives of this compound suppress α-synuclein aggregation by up to 68% at submicromolar concentrations (Biochemical Pharmacology, 2023). The mechanism involves stabilization of microtubule-associated proteins through interactions mediated by the sulfonamide group's protonation state at physiological pH levels.

Toxicological assessments conducted under OECD guidelines confirm an LD?? value exceeding 5 g/kg in rodents when administered orally—a safety profile comparable to conventional pharmaceutical excipients. However, recent metabolomics analyses using LC-MS/MS identified phase II glucuronidation pathways as dominant clearance routes, suggesting potential drug-drug interaction risks when co-administered with CYP3A4 inhibitors.

In conclusion, CAS No. 5317-89-5's structural versatility positions it as an indispensable tool across multiple scientific domains. Ongoing investigations into its epigenetic modulation capabilities and optoelectronic properties promise further breakthroughs, particularly within personalized medicine frameworks where structure-activity relationships can be systematically optimized using AI-driven molecular design platforms.

• 107037-71-8(Methanesulfonamide, N-[4-(3-chloro-1-oxopropyl)phenyl]-)
• 2065-04-5(N-3-(2-bromoacetyl)phenylmethanesulfonamide)
• 73942-52-6(Methanesulfonamide, N,N'-(carbonyldi-4,1-phenylene)bis-)
• 55512-05-5(N-(3-Formylphenyl)methanesulfonamide)
• 5577-42-4(N-4-(2-Bromoacetyl)phenylmethanesulfonamide)
• 107929-91-9(Methanesulfonamide,N-[4-(2-cyanoacetyl)phenyl]-)
• 2417-42-7(N-(3-Acetylphenyl)methanesulfonamide)
• 89264-46-0(Methanesulfonamide, N-(2-amino-5-benzoylphenyl)-)
• 64488-52-4(N-4-(2-Chloroacetyl)phenylmethanesulfonamide)
• 83922-54-7(N-(4-Formylphenyl)methanesulfonamide)