2360-19-2

Usage

Uses

Used in Pharmaceutical Industry:
4-amino-3-nitro-benzenesulfonamide is used as an antibacterial agent for the treatment of urinary tract infections. It was historically significant in this application, although its use has diminished due to the emergence of antibiotic resistance.
Used in Cancer Therapy Research:
4-amino-3-nitro-benzenesulfonamide is used as a subject of investigation in cancer therapy. Its potential role in this field is being explored, leveraging its properties to target cancer cells.
Used in Ophthalmology:
In the treatment of glaucoma, 4-amino-3-nitro-benzenesulfonamide is used as a carbonic anhydrase inhibitor. This application helps in managing the intraocular pressure, a critical factor in glaucoma management.
However, it is important to note that the use of 4-amino-3-nitro-benzenesulfonamide in human medicine has been largely replaced by more effective and less toxic antibiotics, reflecting the evolution of medical treatments and the continuous search for safer and more efficient therapies.

InChI:InChI=1/C6H7N3O4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H,7H2,(H2,8,12,13)

Upstream product

• 39234-94-1 4-acetylamino-3-nitro-benzenesulfonic acid amide 
• 84202-49-3 (2-Nitro-4-sulfamoyl-phenyl)-carbamic acid ethyl ester 
• 41104-55-6 4-(sulfonylphenyl)carbamic acid ethyl ester 
• 63-74-1 sulfanilamide 
• 16761-19-6 4-acetylamino-3-nitro-benzenesulphonyl chloride 
• 97-09-6 4-Chloro-3-nitrobenzenesulfonamide 
• 97-08-5 3-nitro-4-chlorosulfonyl chloride 
• 6668-56-0 4-fluoro-3-nitrobenzene-1-sulfonyl chloride 
• 71905-93-6 acetylaminobenzenesulfonylchloride 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Downstream Products

• 24855-58-1 4-hydroxy-3-nitrobenzenesulfonamide 
• 2360-20-5 3,4-diaminobenzenesulfonamide 
• 32549-07-8 2-Nitro-4-sulfamoyl-benzenesulfonyl chloride 
• 28799-71-5 4-(t-butylamino)-3-nitrobenzenesulfonamide 
• 39234-96-3 4-amino-3-bromo-5-nitrobenzenesulfonamide 
• 27503-84-0 2-phenyl-1H-benzo[d]imidazole-5-sulfonamide 
• 32579-38-7 2-Nitro-benzene-1,4-disulfonic acid 4-(acetyl-amide) 1-dibutylamide 
• 32549-08-9 2-Nitro-benzene-1,4-disulfonic acid 4-amide 1-dibutylamide 
• 78633-55-3 2-Oxo-2,3-dihydro-benzooxazole-5-sulfonic acid (2-amino-4-sulfamoyl-phenyl)-amide 
• 78633-47-3 2-Oxo-2,3-dihydro-benzooxazole-5-sulfonic acid (2-nitro-4-sulfamoyl-phenyl)-amide 

Relevant academic research and scientific papers

Synthesis method of antiviral drug intermediate 4-amino-3-nitrobenzene sulfonamide

The invention relates to a synthesis method of an antiviral drug intermediate 4-amino-3-nitrobenzene sulfonamide. The synthesis method comprises the following steps: taking 4-fluoro-3-nitrobenzene sulfonyl chloride as a main raw material and acetonitrile as a solvent, carrying out ammoniation on ammonia water at room temperature to synthesize the target product 4-amino-3-nitrobenzene sulfonamide by a one-step method, and carrying out low-temperature amination on the intermediate by ammonia water to obtain the target product. The method has the advantages of simple and easily available raw materials, simple and convenient operation, mild synthesis conditions, and good social and economic benefits.

Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors

We describe the synthesis of a series of 2-arylbenzimidazole derivatives bearing sulfonamide functionality (4a–d, 7a–c and 10) as well as hydroxamic acid (15a–b), carboxylic acid (16a–b), carboxamide (17a–b) and boronic acid (22a–b and 26) functionalities, which act as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. The newly synthesized benzimidazole derivatives were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IX, and XII), and especially the sulfonamide-containing benzimidazoles demonstrated intriguing inhibitory activity against tumor associated CA IX and XII with KI values in the range of 5.2–29.3 nM and 9.9–41.7 nM, respectively. Notably, compound 4c was the most potent and selective CA IX (KI = 6.6 nM) and XII (KI = 9.9 nM) inhibitor with a significant selectivity ratio over cytosolic CA I and II isoforms in the range of 3.4–25.2. In addition, compounds having hydroxamic acid (15a-b) or carboxylic acid (16a-b) functionalities resulted in greater selectivity ratios for CA IX/XII over CAI/II in the range of 4.1–121.5 although with KI values in lower micromolar potency (KIs = 0.36–0.85 μM for CA IX/XII).

Synthesis and antistaphylococcal activity of N-substituted-1H- benzimidazole-sulphonamides

A series of N-substituted-1H-benzimidazole-5(6)-sulfonamides and 3-(5,6-dichloro-1H-benzimidazol-2-yl)-N-substituted benzensulfonamides were synthesized and evaluated for antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA). Certain compounds inhibit bacterial growth with low MIC (μg/mL) values. The most active compounds 30, 31, and 32 have the lowest MIC values with 0.39 to 0.19 μg/mL. Among the compounds having sulfonamido moities, 16, 23, and 24 exhibited the strongest antibacterial activity with 1.56 μg/mL MIC values.

2,3-quinoxalinediones for use as neuroleptics

Heterocyclic dihydroxyquinoxaline compounds having the formula STR1 wherein R 1 is hydroxy, alkoxy, aryloxy, aralkyloxy, cycloalkylalkoxy, cycloalkoxy, or acyloxy; andR 5, R 6, R 7 and R 8 independently are hydrogen, NO 2, halogen CN, SO 2 NR''R'', SO 2 R'', CF 3, or OR'', wherein R'' is hydrogen or C 1-4 -alkyl;The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use.The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters, particularly the quisqualate receptors, and especially as neuroleptics.

The Preparation of Sodium 4-Amino-3-nitrobenzenesulfonate and Some Related Compounds

The sodium salt of 4-amino-3-nitrobenzenesulfonic acid (o-nitroaniline-p-sulfonic acid) has been prepared by the action of dilute sodium hydroxide solution on ethyl carbamate.Central to this synthesis is the finding that the N-ethoxycarbonyl group, when located ortho to a nitro group (but not to a bromo group), is readily removed by dilute sodium hydroxide solution.

Substituted benzenesulfonamides as anthelmintics

This invention relates to a novel method for the treatment of parasitic diseases and the compositions used in said treatment. More specifically this invention relates to benzenesulfonamides substituted at the 3, 4, and 5 positions of the benzene ring and to the use of such compounds for the treatment of mature and immature liver fluke infections.