36268-67-4

Usage

Chemical Properties

beige fine crystalline powder

InChI:InChI=1/C8H8N2O2S/c1-13(11,12)10-8-4-2-7(6-9)3-5-8/h2-5,10H,1H3

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 873-74-5 4-Aminobenzonitrile 
• 619-72-7 4-nitrobenzonitrile 
• 7143-01-3 Methanesulfonic anhydride 
• 3144-09-0 methanesulfonamide 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 106307-03-3 2-methoxyethyl 4-mesylaminobenzimidate hydrochloride 
• 129872-50-0 N-<4-(aminomethyl)phenyl>methanesulfonamide 
• 148459-01-2 4-((methylsulfonyl)amino)benzenecarboxamide oxime 
• 128263-66-1 N-<4-(aminomethyl)phenyl>methanesulfonamide hydrochloride 
• 401909-80-6 N-(4-cyano-2-nitrophenyl)methanesulfonamide 
• 4714-65-2 N-butyl-4-aminobenzonitrile 

Relevant academic research and scientific papers

1,2,4-oxadiazol derivatives compound and antiviral agent containing the same as an active ingredient

1, 2, 4 - Oxadiazole derivative compounds and antiviral agents containing the same as an active ingredient. The compound has antiviral activity without cytotoxicity and has antiviral activity, and thus can be useful as an antiviral agent.

Discovery of carboxyl-containing biaryl ureas as potent RORγt inverse agonists

GSK805 (1) is a potent RORγt inverse agonist, but a drawback of 1 is its low solubility, leading to a limited absorption in high doses. We have explored detailed structure-activity relationship on the amide linker, biaryl and arylsulfonyl moieties of 1 trying to improve solubility while maintaining RORγt activity. As a result, a novel series of carboxyl-containing biaryl urea derivatives was discovered as potent RORγt inverse agonists with improved drug-like properties. Compound 3i showed potent RORγt inhibitory activity and subtype selectivity with an IC50 of 63.8 nM in RORγ FRET assay and 85 nM in cell-based RORγ-GAL4 promotor reporter assay. Reasonable inhibitory activity of 3i was also achieved in mouse Th17 cell differentiation assay (76percent inhibition at 0.3 μM). Moreover, 3i had greatly improved aqueous solubility at pH 7.4 compared to 1, exhibited decent mouse PK profile and demonstrated some in vivo efficacy in an imiquimod-induced psoriasis mice model.

Continuous-Flow Electrosynthesis of Benzofused S-Heterocycles by Dehydrogenative C?S Cross-Coupling

Reported herein is the synthesis of benzofused six-membered S-heterocycles by intramolecular dehydrogenative C?S coupling using a modular flow electrolysis cell. The continuous-flow electrosynthesis not only ensures efficient product formation, but also obviates the need for transition-metal catalysts, oxidizing reagents, and supporting electrolytes. Reaction scale-up is conveniently achieved through extended electrolysis without changing the reaction conditions and equipment.

BIARYL UREA DERIVATIVE OR SALT THEREOF, AND MANUFACTURING AND APPLICATION OF SAME

The present invention discloses a biaryl urea RORγt inhibitor, and specifically relates to a biaryl urea derivative, as represented by formula I, with an RORγt inhibiting activity, and a preparation process thereof, and a pharmaceutical composition comprising the compound. Further disclosed is use of the compound for treating an RORγt-related disease.

Soft-Hard Acid/Base-Controlled, Oxidative, N-Selective Arylation of Sulfonanilides via a Nitrenium Ion

In iodine(III)-catalyzed, dehydrogenative arylations of sulfonanilides, the functionalization of C-C bonds is preferred over the functionalization of C-N bonds. Herein, an unprecedented N-selective arylation of sulfonanilides using soft-hard acid-base (SHAB) control by a nitrenium ion over a carbenium ion is reported. Treatment of sulfonanilides with iodine(III) led to the formation of nitrenium ions (soft), which preferentially react with biphenyls (soft) over bimesityl (hard) to generate C-N bonds. The iodine(III) was generated in situ by using PhI and mCPBA at room temperature.

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.

Photochemistry of N-Arylsulfonimides: An Easily Available Class of Nonionic Photoacid Generators (PAGs)

The photochemical behavior of differently substituted N-arylsulfonimides was investigated. Homolysis of the S?N bond took place as the exclusive path from the singlet state to afford both N-arylsulfonamides and photo-Fries adducts, the amount of which depended on reaction conditions and aromatic substituents. Sulfinic and sulfonic acids were released upon irradiation under deaerated and oxygenated conditions, respectively. The nature of the excited states and intermediates involved were proved by laser flash photolysis and EPR experiments. These results highlighted the potential of such compounds as nonionic photoacid generators able to photorelease up to two equivalents of a strong acid for each mole of substrate.

Mild hypervalent iodine mediated oxidative nitration of N-aryl sulfonamides

An oxidative and acid-free method for the nitration of N-aryl sulfonamides has been developed using a combination of sodium nitrite as cheap and easy to handle NO2-source and the hypervalent iodine reagent PIFA as stoichiometric oxidant. Under

Mild Pd-catalyzed N -arylation of methanesulfonamide and related nucleophiles: Avoiding potentially genotoxic reagents and byproducts

A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides is reported. The use of this method eliminates concern over genotoxic impurities that can arise when an aniline is reacted with methanesulfonyl chloride. The application of this method to the synthesis of dofetilide is also reported.

Convenient synthesis of primary sulfonamides

An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.