3989-50-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(Acetylamino)benzenesulfonic acid hydrazide is used as an intermediate in the production of pharmaceuticals for its ability to be incorporated into various drug molecules, contributing to the development of new medications.
Used in Dye Industry:
4-(Acetylamino)benzenesulfonic acid hydrazide is used as an intermediate in the production of dyes, where its chemical structure allows for the creation of a range of colored compounds for various applications.
Used as a Corrosion Inhibitor:
4-(Acetylamino)benzenesulfonic acid hydrazide is used as a corrosion inhibitor in industrial applications, helping to protect materials from degradation and extending their lifespan.

InChI:InChI=1/C8H11N3O3S/c1-6(12)10-7-2-4-8(5-3-7)15(13,14)11-9/h2-5,11H,9H2,1H3,(H,10,12)

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 121-62-0 N-acetylsulfanilic acid 
• 401584-36-9 C₁₃H₁₉N₃O₅S 
• 103-84-4 Acetanilid 

Downstream Products

• 6289-97-0 furfural-[(N-acetyl-sulfanilyl)-hydrazone] 
• 35285-72-4 N-(N-acetyl-sulfanilyl)-N'-nicotinoyl hydrazine 
• 5448-80-6 3-{1-[(N-acetyl-sulfanilyl)-hydrazono]-ethyl}-dihydro-furan-2-one 
• 100396-47-2 5-nitro-furfural-[(N-acetyl-sulfanilyl)-hydrazone] 
• 109562-19-8 1-benzo[b]thiophen-3-yl-ethanon-[(N-acetyl-sulfanilyl)-hydrazone] 
• 5448-90-8 piperonal-[(N-acetyl-sulfanilyl)-hydrazone] 
• 80414-98-8 N'N'-diacetyl p-acetamidobenzenesulfonohydrazide 
• 92327-86-1 4-Acetamino-benzolsulfonsaeure-N'-(1-ethoxycarbonylmethyl-ethyliden)-hydrazid 
• 2408-99-3 N-(N-acetyl-sulfanilyl)-N'-benzoyl-hydrazine 
• 102291-68-9 1-(N-acetyl-sulfanilyl)-4-phenyl thiosemicarbazide 
• 5448-64-6 N-acetyl-sulfanilic acid propylidenehydrazide 
• 80414-97-7 N-acetyl-N'-(N-acetyl-sulfanilyl)-hydrazine 
• 860002-19-3 1-(N-acetyl-sulfanilyl)-4-methyl thiosemicarbazide 
• 115122-67-3 1-(N-acetyl-sulfanilyl)-4-[1]naphthyl thiosemicarbazide 

Relevant academic research and scientific papers

Inhibition of carbonic anhydrase II by sulfonamide derivatives

A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.

Novel Schiff base-bridged multi-component sulfonamide imidazole hybrids as potentially highly selective DNA-targeting membrane active repressors against methicillin-resistant Staphylococcus aureus

A new type of Schiff base-bridged multi-component sulfonamide imidazole hybrids with antimicrobial potential was developed. Some target compounds showed significant antibacterial potency. Observably, butylene hybrids 4h exhibited remarkable inhibitory efficacy against clinical MRSA (MIC = 1 μg/mL), but had no significant toxic effect on normal mammalian cells (RAW 264.7). The highly active molecule 4h was revealed by molecular modeling study that it could insert into the base-pairs of DNA hexamer duplex and bind with the ASN-62 residue of human carbonic anhydrase isozyme II through hydrogen bonding. Furthermore, further preliminary antibacterial mechanism experiments confirmed that compound 4h could effectively interfere with MRSA membrane and insert into bacterial DNA isolated from clinical MRSA strains through non-covalent bonding to produce a supramolecular complex, thus exerting its strong antibacterial efficacy by impeding DNA replication. These findings strongly implied that the highly active hybrid 4h could be used as a potential DNA-targeting template for the development of valuable antimicrobial agent.

Synthesis and Antibacterial Activity of Sulfanilamides Containing Sterically Hindered Phenol Fragments

Abstract: New sulfanilamide derivatives containing sterically hindered phenol fragments have been synthesized via modification of the amino group by reaction with 3,5-di-tert-butyl-4-hydroxybenzyl acetate and diazotization followed by diazo coupling with

SAR study of 4-arylazo-3,5-diamino-1: H -pyrazoles: identification of small molecules that induce dispersal of Pseudomonas aeruginosa biofilms

By screening of a collection of 50 000 small-molecule compounds, we recently identified 4-arylazo-3,5-diamino-1H-pyrazoles as a novel group of anti-biofilm agents. Here, we report a SAR study based on 60 analogues by examining ways in which the pharmacoph

NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions

We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).

One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water

A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.

Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II

Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.

TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?

A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.

Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides

Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.

Synthesis of calix[4]azacrown substituted sulphonamides with antioxidant, acetylcholinesterase, butyrylcholinesterase, tyrosinase and carbonic anhydrase inhibitory action

A series of novel calix[4]azacrown substituted sulphonamide Schiff bases was synthesised by the reaction of calix[4]azacrown aldehydes with different substituted primary and secondary sulphonamides. The obtained novel compounds were investigated as inhibitors of six human (h) isoforms of carbonic anhydrases (CA, EC 4.2.1.1). Their antioxidant profile was assayed by various bioanalytical methods. The calix[4]azacrown substituted sulphonamide Schiff bases were also investigated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase enzymes, associated with several diseases such as Alzheimer, Parkinson, and pigmentation disorders. The new sulphonamides showed low to moderate inhibition against hCAs, AChE, BChE, and tyrosinase enzymes. However, some of them possessed relevant antioxidant activity, comparable with standard antioxidants used in the study.