7022-24-4

Upstream product

• 536-90-3 m-Anisidine 
• 124-63-0 methanesulfonyl chloride 
• 10365-98-7 3-methoxyphenylboronic acid 
• 624-90-8 Methanesulfonyl azide 
• 1548871-62-0 C₉H₁₁NO₅S 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 108297-27-4 N-(5-Methoxy-2,4-bis-pyrrolidin-1-ylmethyl-phenyl)-methanesulfonamide 
• 210714-08-2 N-(3-Methoxy-phenyl)-N-(2-oxo-propyl)-methanesulfonamide 
• 210714-05-9 N-(3-Methoxy-phenyl)-N-(3-triisopropylsilanyl-prop-2-ynyl)-methanesulfonamide 
• 1447967-41-0 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)methanesulfonamide 
• 1447967-48-7 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)methanesulfonamide 
• 6931-19-7 5-methoxyquinoline 
• 4964-76-5 7-methoxyquinoline 
• 333383-78-1 N-(3-methoxy-phenyl)-N-(3-oxo-propyl)-methanesulfonamide 
• 88156-69-8 N-(2,2-Diethoxy-ethyl)-N-(3-methoxy-phenyl)-methanesulfonamide 

Relevant academic research and scientific papers

Electrosynthesis of sulfonamides from DMSO and amines under mild conditions

With DMSO as the solvent and the precursor of a -SO2Me unit at room temperature, a novel electrochemical oxidization and amination of DMSO with amines was developed for the synthesis of sulfonamides. Our investigations reveal that this transformation may involve a radical process and an electrochemical oxidization of DMSO.

Facile Chan-Lam coupling using ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene

Ferrocene tethered N-heterocyclic carbene-copper complex anchored on graphene ([GrFemImi]NHC@Cu complex) has been synthesized by covalent grafting of ferrocenyl ionic liquid in the matrix of graphene followed by metallation with copper (I) iodide. The [GrFemImi]NHC@Cu complex has been characterized by fourier transform infrared (FT-IR), fourier transform Raman (FT-Raman), CP-MAS 13C NMR spectroscopy, transmission electron microscopy (TEM), thermogravimetric analysis (TGA), energy dispersive X-ray (EDX) analysis, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET) surface area analysis and X-ray diffractometer (XRD) analysis. This novel complex served as a robust heterogeneous catalyst for the synthesis of bioactive N-aryl sulfonamides from variety of aryl boronic acids and sulfonyl azides in ethanol by Chan-Lam coupling. Recyclability experiments were executed successfully for six consecutive runs.

1,3,4-OXADIAZOLE SULFONAMIDE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to novel compounds represented by the formula I having histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, the use thereof for the preparation of therapeutic medicaments, pharmaceutical compositions containing the same, a method for treating diseases using the composition, and methods for preparing the novel compounds. (I) The novel compounds, stereoisomers thereof or pharmaceutically acceptable salts thereof according to the present invention have histone deacetylase (HDAC) inhibitory activity and are effective for the prevention or treatment of HDAC6-mediated diseases.

Synthesis and anti-cancer activities of new sulfonamides 4-substituted-triazolyl nucleosides

Nucleoside analogues are among the most known drugs commonly used in antiviral and anticancer chemotherapies. Among them, those featuring a five-membered ring nucleobase are of utmost interest such as the anti-cancer agent AICAR or the anti-viral drug ribavirin. Despite its low activity in vitro in different cell lines, AICAR is under clinical development for several pathologies, thanks to its original mode of action. Indeed, AICAR induced autophagy cell death and is able, following this mechanism, to circumvent resistance to apoptotic drugs including kinase inhibitors currently on the market. To improve the activity of AICAR, we report herein an efficient synthesis of new series of sulfonamide-4-substituted-1,2,3-triazolyl nucleosides using a Cu-catalyzed 1,3-dipolar cycloaddition. All these molecules have been fully characterized and evaluated against two aggressive tumor cell lines, RCC4 and MDA-MB-231. Among them, nucleoside analogue 5i belonging to the ribose series was found to be 19 to 66-fold more active than AICAR. Western blot analyses on RCC4 cells showed that 5i displayed an interesting mode of action by inducing both apoptosis and autophagy cell death, making therefore this class of molecules highly promising for further hit-to-lead optimization.

Palladium-Catalyzed cascade sp2 c?H bond functionalizations allowing one-Pot access to 4?Aryl-1,2,3,4-tetrahydroquinolines from n?Allyl?N?arylsulfonamides

We have developed a palladium-catalyzed cascade reaction allowing an efficient synthesis of 4-aryl-1,2,3,4-tetrahydroquinolines from N-allyl-N-arylsulfonamides and benzenesulfonyl chlorides. In this transformation, two C(sp2)?C(sp3) bonds were formed via activation of C(sp2)?H bonds. The reaction proceeds using the easily accessible catalyst PdCl2, with Li2CO3 as inexpensive base and CuBr as additive, and tolerates a wide variety of substituents on both reaction partners.

Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation

The Ir-catalyzed mild C-H amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional-group compatibility. Subsequent protodecarboxylation of ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)aniline derivatives, the latter being inaccessible by other C-H functionalization approaches. The decarboxylation step was compatible with the amidation conditions, enabling a convenient one-pot, two-step process. Without a trace: Carboxylic acids are used as traceless directing groups in the Ir-catalyzed direct C-H amidation of arenes with sulfonyl azides under mild conditions. The tandem protodecarboxylation of the ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)anilines, which are difficult to obtain by other C-H functionalization approaches.

Copper-catalyzed Chan-Lam Coupling between Sulfonyl Azides and Boronic acids at room temperature

A mild and efficient method for the synthesis of N-arylsulfonamides in the presence of 10 mol % of CuCl is demonstrated. The reaction proceeds readily at room temperature in an open flask using a variety of sulfonyl azides and boronic acids without any base, ligand, or additive.

Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent

A scalable synthesis of the neuroprotective agent P7C3-A20 is described. The synthesis has provided hundred-gram batches of the final compound for biological evaluation in rodents primates. The synthesis can be performed without chromatographic purificati

A practical route to quinolines from anilines

A practical route to quinoline from anilines through acid-mediated cyclization of 3-(N-aryl-N-sulfonylamino)propionaldehydes has been developed. Treatment of the cyclization products, dihydroquinoline intermediates with KOH in DMSO leads to substituted quinolines.