83922-51-4

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-Bromophenyl)methansulfonamide is used as a building block for the synthesis of pharmaceuticals due to its ability to contribute to the development of molecules with anti-inflammatory and analgesic effects. Its incorporation into drug formulations can lead to the creation of new treatments for a variety of inflammatory and pain-related conditions.
Used in Organic Synthesis:
In the field of organic synthesis, N-(3-Bromophenyl)methansulfonamide is utilized as a reagent for the modification of other molecules. Its chemical properties allow it to participate in various synthetic pathways, potentially enhancing the properties of target compounds or aiding in the synthesis of complex organic molecules.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 591-19-5 m-Bromoaniline 

Downstream Products

• 4964-71-0 5-bromoquinoline 
• 875917-18-3 N-(3-bromophenyl)-N-methylmethanesulfonamide 
• 1314806-75-1 C₁₃H₁₉NO₂SSi 
• 1314806-76-2 N-(3-ethynylphenyl)-N-methylmethanesulfonamide 
• 597561-37-0 N-(3-cyanophenyl)-N-methylmethanesulfonamide 
• 305448-92-4 N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide 

Relevant academic research and scientific papers

BTK Inhibitors and uses thereof

The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.

Design, synthesis, biological evaluation and molecular docking study of novel thieno[3,2-d]pyrimidine derivatives as potent FAK inhibitors

A series of 2,7-disubstituted-thieno[3,2-d]pyrimidine derivatives were designed, synthesized and evaluated as novel focal adhesion kinase (FAK) inhibitors. The novel 2,7-disubstituted-thieno[3,2-d]pyrimidine scaffold has been designed as a new kinase inhibitor platform that mimics the bioactive conformation of the well-known diaminopyrimidine motif. Most of the compounds potently suppressed the enzymatic activities of FAK and potently inhibited the proliferation of U-87MG, A-549 and MDA-MB-231 cancer cell lines. Among these derivatives, the optimized compound 26f potently inhibited the enzyme (IC50 = 28.2 nM) and displayed stronger potency than TAE-226 in U-87MG, A-549 and MDA-MB-231 cells, with IC50 values of 0.16, 0.27, and 0.19 μM, respectively. Compound 26f also exhibited relatively less cytotoxicity (IC50 = 3.32 μM) toward a normal human cell line, HK2. According to the flow cytometry results, compound 26f induced the apoptosis of MDA-MB-231 cells in a dose-dependent manner and effectively arrested MDA-MB-231 cells in G0/G1 phase. Further investigations revealed that compound 26f potently suppressed the migration of MDA-MB-231 cells. Collectively, these data support the further development of compound 26f as a lead compound for FAK-targeted anticancer drug discovery.

Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds

A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.

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.

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.

3-(PYRAZOLYL)-1H-PYRROLO[2,3-b]PYRIDINE DERIVATIVES AS KINASE INHIBITORS

The present application relates to novel 3-(pyrazolyl)-lH-pyrrolo[2,3-b]pyridine derivatives of formula (I), as protein kinase inhibitors. The invention particularly relates to compounds of formula (I), preparation of compounds and pharmaceutical compositions thereof. The invention further relates to pharmaceutically acceptable salts and compositions comprising the said novel 3-(pyrazolyl)-lH-pyrrolo[2,3-b]pyridine derivatives and their use in the treatment of various disorders.

Triazole-linked reduced amide isosteres: An approach for the fragment-based drug discovery of anti-Alzheimer's BACE1 inhibitors

In the course of a β-site APP-cleaving enzyme 1 (BACE1) inhibitor discovery project an in situ synthesis/screening protocol was employed to prepare 120 triazole-linked reduced amide isostere inhibitors. Among these compounds, four showed modest (single digit micromolar) BACE1 inhibition. Our ligand design was based on a potent reduced amide isostere 1, wherein the P 2 amide moiety was replaced with an anti-1,2,3-triazole unit. Unfortunately, this replacement resulted in a 1000-fold decrease in potency. Docking studies of triazole-linked reduced amide isostere A3Z10 and potent oxadiazole-linked tertiary carbinamine 2a with BACE1 suggests that the docking poses of A3Z10 and 2a in the active sites are quite similar, with one exception. In the docked structures the placement of the protonated amine that engages D228 differs considerably between 2a and A3Z10. This difference could account for the lower BACE1 inhibition potency of A3Z10 and related compounds relative to 2a.

Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-free conditions without using external base

Microwave-induced syntheses of sulfonamides, without using base under solvent-free conditions, have been developed. The process finds its utility because of its simple operational procedure and high yields. Moreover, the process is fast and accommodative to different substituents on aromatic as well as heteroaromatic rings rendering sulfonamides (28 examples).

N-HYDROXYFORMAMIDE DERIVATIVES AS INHIBITORS OF MATRIX METALLOPROTEINASES

Compounds having formula (I) are matrix metalloproteinase inhibitors. Also disclosed are matrix metalloproteinase-inhibiting compositions and methods of inhibiting matrix metalloproteinase in a mammal.

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.