1565-17-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Acetylbenzenesulphonamide is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Research and Development:
4-Acetylbenzenesulphonamide is used as a research tool in the study of pharmacokinetics, particularly in characterizing the behavior of reversible drug-metabolite systems. This application helps researchers understand the interactions between drugs and their metabolites, which is crucial for the development of more effective and safer medications.

InChI:InChI=1/C8H9NO3S/c1-6(10)7-2-4-8(5-3-7)13(9,11)12/h2-5H,1H3,(H2,9,11,12)

Upstream product

• 5335-82-0 1,1'-(disulfane-1,2-diylbis(4,1-phenylene))bis(ethan-1-one) 
• 98-61-3 p-Iodobenzenesulfonyl chloride 
• 97674-02-7 tributyl(1-ethoxyvinyl)stannane 
• 98-58-8 4-bromobenzenesulfonyl chloride 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 99-92-3 p-aminobenzophenone 
• 3283-79-2 4-acetylphenyldiazonium chloride 
• 16712-69-9 p-ethylbenzenesulfonyl chloride 
• 778592-00-0 4-acetyl-N-isopropylbenzenesulfonamide 
• 204389-55-9 N-tert-butyl-4-acetylbenzenesulfonamide 
• 1788-10-9 4-Acetylbenzenesulfonyl chloride 
• 138-38-5 4-ethylbenzenesulfonamide 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 

Downstream Products

• 128924-64-1 C₁₅H₁₃ClN₂O₄S 
• 170570-95-3 4-Acetyl-N,N-bis-(4-methoxy-benzyl)-benzenesulfonamide 
• 113412-15-0 (+/-)-4-(1-hydroxyethyl)benzenesulfonamide 
• 552845-21-3 4-[3E-(5-BENZO[b]THIOPHEN-2-YL-2,4-DIMETHOXYPHENYL)ACRYLOYL]benzenesulfonamiode 
• 944-33-2 2-bromo-4'-aminosulfonylacetophenone 
• 75177-14-9 4-acetylbenzenesulfonyl azide 
• 1165800-22-5 2-[4-(aminosulfonyl)phenyl]quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Simple and efficient synthesis of 3,4-dihydro-2-pyridones via novel solid-supported aza-annulation

A diverse array of 3,4-dihydro-2-pyridones 13 were produced utilizing the unique properties of solid-supported reactions to both drive the reactions to completion and isolate the desired products. The pyridones were synthesized in high purity by a simple sequence of novel steps commencing from an acetophenone-functionalized resin. The para-substituted acetophenone 9 could be anchored to the resin through either a sulfonamide or a carboxamide linkage. The sulfonamide resin 9a, which gave the best results, was treated with several aryl aldehydes and ethoxide to give a variety of chalcones 10a-k in excellent yield (82-99%) upon TFA cleavage. Addition of either methyl or allyl malonate and DBU to 10a-k afforded smoothly the Michael adducts 11a-j (70-99%) which were subsequently cyclized in one step employing acetic acid as a catalyst and several diverse amines to give pure 3,4-dihydro-2-pyridones 13a-p in moderate to excellent yields (30-98%).

Optimization of Hydantoins as Potent Antimycobacterial Decaprenylphosphoryl-β-d-Ribose Oxidase (DprE1) Inhibitors

In search of novel drugs against tuberculosis, we previously discovered and profiled a novel hydantoin-based family that demonstrated highly promising in vitro potency against Mycobacterium. tuberculosis. The compounds were found to be noncovalent inhibitors of DprE1, a subunit of decaprenylphosphoryl-β-d-ribose-2′-epimerase. This protein, localized in the periplasmic space of the mycobacterial cell wall, was shown to be an essential and vulnerable antimycobacterial drug target. Here, we report the further SAR exploration of this chemical family through more than 80 new analogues. Among these, the most active representatives combined submicromolar cellular potency and nanomolar target affinity with balanced physicochemical properties and low human cytotoxicity. Moreover, we demonstrate in vivo activity in an acute Mtb infection model and provide further proof of DprE1 being the target of the hydantoins. Overall, the hydantoin family of DprE1 inhibitors represents a promising noncovalent lead series for the discovery of novel antituberculosis agents.

Palladium-Catalyzed ortho-Benzoylation of Sulfonamides through C?H Activation: Expedient Synthesis of Cyclic N-Sulfonyl Ketimines

The ortho-carbonylation of sulfonylarenes by non-hazardous aryl aldehydes as a carbonyl precursor was reported. In this method, the sulfonamide group serves as a directing group for C?H activation in the presence of a Pd catalyst under ligand-free conditions. The scope of this strategy has been extended to the one-pot two-step synthesis of cyclic N-sulfonyl ketimines under mild reaction conditions. Our approach could be considered as an alternative by circumventing the use of highly reactive organolithium or Grignard reagents to access a wide range of biologically potent cyclic N-sulfonyl ketimines. (Figure presented.).

Design, Synthesis, and Biological Evaluation of Novel Allosteric Protein Disulfide Isomerase Inhibitors

Protein disulfide isomerase (PDI) is responsible for nascent protein folding in the endoplasmic reticulum (ER) and is critical for glioblastoma survival. To improve the potency of lead PDI inhibitor BAP2 ((E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile), we designed and synthesized 67 analogues. We determined that PDI inhibition relied on the A ring hydroxyl group of the chalcone scaffold and cLogP increase in the sulfonamide chain improved potency. Docking studies revealed that BAP2 and analogues bind to His256 in the b′ domain of PDI, and mutation of His256 to Ala abolishes BAP2 analogue activity. BAP2 and optimized analogue 59 have modest thiol reactivity; however, we propose that PDI inhibition by BAP2 analogues depends on the b′ domain. Importantly, analogues inhibit glioblastoma cell growth, induce ER stress, increase expression of G2M checkpoint proteins, and reduce expression of DNA repair proteins. Cumulatively, our results support inhibition of PDI as a novel strategy to treat glioblastoma.

Sulfonamide compound and synthesis method and application thereof

The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.

Metal-free construction of primary sulfonamides through three diverse salts

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.

PYRROLE DERIVATIVES AS PLK1 INHIBITORS

The invention provides compounds of the formula (3): or a pharmaceutically acceptable salt or tautomer thereof. The compounds are useful in the treatment of cancers.

HETEROCYCLIC COMPOUNDS AS JAK RECEPTOR AND PROTEIN TYROSINE KINASE INHIBITORS

The invention relates to compounds of general formula (I) wherein A, R1, R2, R3, R4, R5, R9, m and n are defined as defined herein, and pharmaceutically acceptable salts, hydrates, or solvates thereof, for use -alone or in combination with one or more other pharmaceutically active compounds- in therapy, as JAK kinase and protein tyrosine kinase inhibitors for preventing, treating or ameliorating diseases and complications thereof, including, for example, psoriasis, atopic dermatitis, rosacea, lupus, multiple sclerosis, rheumatoid arthritis, Type I diabetes, asthma, cancer, autoimmune thyroid disorders, ulcerative colitis, Crohn's disesase, Alzheimer's disease, leukaemia, eye diseases such as diabetic retinopathy and macular degeneration as well as other autoimmune diseases and indications where immunosuppression would be desirable for example in organ transplantation.

PYRAZINE DERIVATIVES AND USE AS PI3K INHIBITORS

The present invention is related to pyrazine derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

Scandium triflate as an efficient and recyclable catalyst for the deprotection of tert-butyl aryl sulfonamides

A mild and efficient method for deprotection of tert-butyl sulfonamide groups utilizing Sc(OTf)3 as deprotecting reagent has been developed. A variety of tert-butyl aryl sulfonamides used under these conditions gave the corresponding primary sulfonamides in high yields. The Lewis acid catalyst could be fully recovered and reused with maintained activity after the reactions. Copyright Taylor & Francis, Inc.