6794-84-9

Upstream product

• 6822-80-6 (4-benzooxazol-2-ylsulfamoyl-phenyl)-carbamic acid methyl ester 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 6846-56-6 4-acetylamino-N-benzooxazol-2-yl-benzenesulfonamide 
• 4570-41-6 1,3-benzoxazol-2-amine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 24939-24-0 4-aminobenzenesulfonyl chloride 
• 21926-53-4 4-methoxycarbonylamino-benzenesulfonyl chloride 
• 2651-14-1 Dimethyl N-(4-Aminophenylsulphonyl)dithiocarbonimidate 
• 95-55-6 2-amino-phenol 

Downstream Products

• 6885-19-4 4-amino-N-benzooxazol-2-yl-benzenesulfonamide; compound with diethylamine (1:1) 

Relevant academic research and scientific papers

The optimization and characterization of functionalized sulfonamides derived from sulfaphenazole against Mycobacterium tuberculosis with reduced CYP 2C9 inhibition

In this study, a series of sulfonamide compounds was designed and synthesized through the systematic optimization of the antibacterial agent sulfaphenazole for the treatment of Mycobacterium tuberculosis (M. tuberculosis). Preliminary results indicate that the 4-aminobenzenesulfonamide moiety plays a key role in maintaining antimycobacterial activity. Compounds 10c, 10d, 10f and 10i through the optimization on phenyl ring at the R2 site on the pyrazole displayed promising antimycobacterial activity paired with low cytotoxicity. In particular, compound 10d displayed good activity (MIC = 5.69 μg/mL) with low inhibition of CYP 2C9 (IC50 > 10 μM), consequently low potential risk of drug-drug interaction. These promising results provide new insight into the combination regimen using sulfonamide as one component for the treatment of M. tuberculosis.

Chemical synthesis and molecular modeling of novel substituted N-1,3-benzoxazol-2yl benzene sulfonamides as inhibitors of inhA enzyme and Mycobacterium tuberculosis growth

Abstract: Tuberculosis (TB) is one of the major contagious diseases with high mortality which is caused by Mycobacterium tuberculosis (Mtb) pathogen. Due to the existing antibiotic resistance (MDR-TB) to tuberculosis, the demand for the development of new potential chemotherapy drugs is increasing. Herein, we report synthesis of two novel benzoxazole-based series, namely 2-phenyl benzoxazole sulfonamide and 2-piperidine-benzoxazole sulfonamides. These compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain, using the microplate alamarBlue assay. Molecular docking studies were carried out to comprehend the binding mode of the compounds. It is evident from molecular docking studies and minimum inhibitory concentration assay (MIC) that 2-phenyl benzoxazole sulfonamide scaffold has a greater potential of antitubercular activity possibly by ENR inhibition (inhA inhibitors). In silico cytotoxicity studies using CLC-Pred tool database suggested that both the series were relatively safe. Graphic abstract: [Figure not available: see fulltext.].

Synthesis and structure-activity relationship studies of 4-((2-hydroxy-3-methoxybenzyl)amino)benzenesulfonamide derivatives as potent and selective inhibitors of 12-lipoxygenase

Human lipoxygenases (LOXs) are a family of iron-containing enzymes which catalyze the oxidation of polyunsaturated fatty acids to provide the corresponding bioactive hydroxyeicosatetraenoic acid (HETE) metabolites. These eicosanoid signaling molecules are involved in a number of physiologic responses such as platelet aggregation, inflammation, and cell proliferation. Our group has taken a particular interest in platelet-type 12-(S)-LOX (12-LOX) because of its demonstrated role in skin diseases, diabetes, platelet hemostasis, thrombosis, and cancer. Herein, we report the identification and medicinal chemistry optimization of a 4-((2-hydroxy-3-methoxybenzyl)amino) benzenesulfonamide-based scaffold. Top compounds, exemplified by 35 and 36, display nM potency against 12-LOX, excellent selectivity over related lipoxygenases and cyclooxygenases, and possess favorable ADME properties. In addition, both compounds inhibit PAR-4 induced aggregation and calcium mobilization in human platelets and reduce 12-HETE in β-cells.

Functionalized azoles and triazolo[1,5-a]pyrimidines as latent leishmanicides

Triazolo[1,5-a]pyrimidine (3-6), benzoxazole (7a,b) and benzimidazole (7c) derivatives have been synthesized and evaluated for their in vitro leishmanicidal activity against L. donovani promastigotes.

Diheterocyclic Compounds from Dithiocarbamates and Derivatives Thereof. VI. Unsymmetrical N1,N4-Bis(2-benzazolyl)sulphanilamides

The title compounds 9 are readily synthesized from dithiocarbamic acid derivative 5 by stepwise formation of the heterocyclic rings.Differences in reactivity of dithiocarbamates and dithiocarbonimidates make group protection unnecessary.