54734-84-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromobenzenesulfonamide is used as an intermediate in the synthesis of pharmaceuticals, particularly for the development of anti-inflammatory and antiviral drugs. Its unique structure and properties make it a valuable component in creating effective medications.
Used in Dye and Pigment Production:
In the dye and pigment industry, 2-Amino-5-bromobenzenesulfonamide is utilized in the production of various dyes and pigments. Its chemical properties contribute to the creation of a wide range of colors and hues, enhancing the vibrancy and quality of the final products.

InChI:InChI=1/C6H7BrN2O2S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3H,8H2,(H2,9,10,11)

Upstream product

• 3306-62-5 2-AMINOBENZENESULFONAMIDE 
• 14141-71-0 7-bromo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 
• 106-40-1 4-bromo-aniline 
• 89599-01-9 3-bromobenzenesulfonamide 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 5455-59-4 2-Nitrobenzenesulfonamide 

Downstream Products

• 37162-46-2 7-bromo-2(4)H-benzo[e][1,2,4]thiadiazin-1,1-dioxide 
• 14141-71-0 7-bromo-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide 
• 37162-46-2 7-bromo-4H-1,2,4-benzothiadiazine 1,1-dioxide 
• 686265-42-9 N-[2-(aminosulfonyl)-4-bromophenyl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide 
• 686266-22-8 N-[2-(aminosulfonyl)phenyl]-1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide 
• 686267-53-8 N-[2-(aminosulfonyl)phenyl]-4-hydroxy-1-isobutoxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide 
• 690959-90-1 N-[2-(aminosulfonyl)phenyl]-4-hydroxy-2-oxo-1-propoxy-1,2-dihydroquinoline-3-carboxamide 
• 690959-94-5 N-[2-(aminosulfonyl)-5-chlorothien-3-yl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide 
• 690959-93-4 N-[2-(aminosulfonyl)-5-chlorothien-3-yl]-1-benzyl-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxamide 
• 1292302-74-9 5-bromo-2-(3-methylbutyrylamino)benzenesulfonamide 
• 1349036-73-2 7-bromo-3-(3-methylphenyl)-4H-1,2,4-benzothiadiazine-1,1-dioxide 
• 959461-43-9 C₈H₄BrF₃N₂O₂S 

Relevant academic research and scientific papers

FUSED [1,2,4]THIADIAZINE DERIVATIVES WHICH ACT AS KAT INHIBITORS OF THE MYST FAMILY

A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1 and MOF.

Iridium-Catalyzed ortho-C?H Amidation of Benzenesulfonamides with Sulfonyl Azides

We developed herein an iridium-catalyzed direct C?H activation/ C?N bond formation reaction of benzenesulfonamides with sulfonyl azides. The amidation reaction provides a protocol for the synthesis of 2-aminobenzesulfonamides in good to excellent yields. This strategy features a wide substrate scope, tolerates a broad range of functional groups under external oxidant-free conditions and only releases molecular nitrogen as the sole by-product. Moreover, the preliminary mechanism was investigated and the proposed reaction pathway was provided. (Figure presented.).

1. 1 - dioxo - 4H - benzo [1, 2, 4] - thiadiazine hydrochloric acid salt compound and its preparation method

The invention discloses a 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound and a preparation method thereof, belonging to the technical field of organic synthesis. The technical scheme has the key point as follows: the 1,1-dioxo-4H-benzo[1,2,4]- thiadiazine hydrochloride compound has the structure as shown in the specification, wherein R is H, -CH3 or -C2H5. The invention also discloses the preparation method of the 1,1-dioxo-4H-benzo[1,2,4]-thiadiazine hydrochloride compound. The preparation method is simple, convenient and easy to operate, relatively high in reaction efficiency and relatively good in repeatability, and raw materials are cheap and available.

FUSED RING COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

Provided are fused tricyclic compounds effective to inhibit the function of the NS5A protein of formula (I), wherein X, X', Y, Y', A, A',Q1, Q2, R1-R4, X4, R5a, f and W are defined as in the description. Also provided herein are pharmaceutical compositions thereof, and uses in the manufacture of a medicament for treating HCV infection or a HCV disorder thereof.

Integrated structure-based activity prediction model of benzothiadiazines on various genotypes of HCV NS5b polymerase (1a, 1b and 4) and its application in the discovery of new derivatives

This work presents the first structure-based activity prediction model for benzothiadiazines against various genotypes of HCV NS5b polymerase (1a, 1b and 4).The model is a comprehensive workflow of structure-based field template followed by guided docking. The field template was used as a pre-filter and a tool to provide hits in good orientation and position. It was created based on detailed molecular interaction field analysis which includes Topomer CoMFA, grid independent analysis and Superstar. On the other hand, Guided docking was used as a refinement and assessment tool. It was actively directed by two scores: Moldock score as an interaction descriptor (r2 = 0.65) and a template similarity score as a measure for accurate binding-mode compliance. The docking template was based on energy-based pharmacophore analysis. The whole procedure was formulated and tweaked for both screening (ROC of AUC = 0.91) and activity prediction (r2 of 0.8) for the genotype 1a. In order to widen the model scope, linear interaction energy was used as a tool for predicting activities of other genotypes based on the docked ligand poses while mutation binding energy was used to investigate the effect of each amino acid mutation in genotype 4. The model was applied for structure-based fragment hopping by screening a library designed by reaction enumeration. A top scoring hit was used to generate a focused library such that it has lower TPSA than the original class ligands and thus better pharmacokinetic properties. After that, experimental validation was carried out by the synthesis of this library and its biological evaluation which yielded compounds that exhibit EC50 ranging from 1.86 to 23 μM.

Acetic acid derivatives of 3,4-dihydro-2 H-1,2,4-benzothiadiazine 1,1-dioxide as a novel class of potent aldose reductase inhibitors

A series of novel benzothiadiazine 1,1-dioxide derivatives were synthesized and tested for their inhibitory activity against aldose reductase. Of these derivatives, 17 compounds, having a substituted N2-benzyl group and a N4-acetic acid group on the benzothiadiazine, were found to be potent and selective aldose reductase inhibitors in vitro with IC50 values ranging from 0.032 to 0.975 μM. 9m proved to be the most active in vitro. The eight top-scoring compounds coming from the in vitro test for ALR2 inhibition activity were then tested in vivo, whereby three derivatives, 9i, 9j, and 9m, demonstrated a significantly preventive effect on sorbitol accumulation in the sciatic nerve in the 5-day streptozotocin-induced diabetic rats in vivo. Structure-activity relationship and molecular docking studies highlighted the importance of substitution features of N4-acetic acid group and halogen-substituted N2-benzyl group in the benzothiadiazine scaffold and indicated that substitution with hallogen at C-7 had a remarkably strong effect on ALR2 inhibition potency.

Structure-activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors

The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents.

Inhibitors of HCV NS5B polymerase: Synthesis and structure-activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring

A series of non-nucleoside HCV NS5B polymerase inhibitors based on the N-1-benzyl or N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine core substituted in the D-ring aromatic moiety have been prepared and evaluated. Aromatic substituents extending from position 7 of the D-ring exhibited excellent potency against both genotypes 1a and 1b.

Anti-infective agents

Compounds having the formula are hepatitis C(HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C(HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.