2067-06-3

Basic information

• Product Name: 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzenesulfonamide
• CAS NO: 2067-06-3
• Molecular Formula: C₁₃H₁₂N₂O₃S
• Molecular Weight: 276.311
• Mol File: 2067-06-3.mol

Chemical Properties

• Boiling Point: 507.2°C at 760 mmHg
• Flash Point: 260.5°C
• Density: 1.509g/cm³
• Vapor Pressure: 2.08E-10mmHg at 25°C
• Refractive Index: 1.726
• CAS DataBase Reference: 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzenesulfonamide(2067-06-3)
• EPA Substance Registry System: 4-{[(6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino}benzenesulfonamide(2067-06-3)

Safety Data

• Hazardous Substances Data: 2067-06-3(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 63-74-1 sulfanilamide 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 13159-86-9 2-hydroxybenzyl (4'-aminosulfonylphenyl) amine 
• 121723-57-7 {Sn(C₄H₉)3C₁₃H₁₁N₂O₃S} 
• 128711-74-0 {Ni(OC₆H₄CHNC₆H₄SO₂NH₂)2} 
• 113971-43-0 Sm(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-44-1 Eu(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-42-9 Nd(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-39-4 La(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-41-8 Pr(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-40-7 Ce(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113986-77-9 Tm(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-49-6 Er(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-50-9 Yb(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-51-0 Lu(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 
• 113971-48-5 Ho(H₂NSO₂C₆H₄NCHC₆H₄O)3(H₂O)2 

Relevant articles and documents

An old oxovanadium(IV) complex of N-(salicylidene)sulfanilamide: theoretical validity of experimental observations

Sulfa drug Schiff base complexes of oxovanadium are counted among highly significant molecular scaffolds of industrial and medicinal relevance. In order to present a theoretical validation of our earlier reported complex of this sort herein, a comparative

Synthesis, characterization, biological evaluation, and molecular docking approach of nickel (II) complexes containing O, N-donor chelation pattern of sulfonamide-based Schiff bases

A series of Schiff bases (L1–L4) that possess in their structure bioactive sulfonamide group and their nickel (II) complexes have been synthesized. Microanalytical analyses, various spectroscopic methods such as Fourier transform infrared spectroscopy (FT-IR), 1H nuclear magnetic resonance (NMR), 13C NMR, UV–Vis, and MS, are used to explore the nature of bonding and to elucidate the chemical structures. The analytical and magnetic values suggest a range of stoichiometries 1:1, 1:2, and 2:1 (M:L) for the synthesized complexes of almost square planar geometry. The spectral comparative interpretation reveals that L1 and L2 coordinate to the central Ni (II) in tetradentate ONON donor sequence, whereas L3 and L4 in bidentate ON pattern through deprotonated phenolic-O and the azomethine-N. Density functional theory (DFT) and MOE-docking approaches are used to evaluate the molecular parameters and the binding propensity of the synthesized ligands and their complexes with 3s7s protein and to signify their inhibition strength. Besides, the anticancer, antimicrobial and antifungal activities have been screened against number of tumor cells and human pathogen strains. These in vitro studies reveal that Schiff base L4 and its complex, [Ni(L4-H)(OAc)(H2O)], have superior activities reflecting the importance of inserting bioactive pendant substituents such as thiazole ring and 3-fluorophenylazo to the pharmacophoric sulfonamide moiety. Moreover, some of the synthesized Ni (II) complexes display promising therapeutic effects as novel non-platinum antitumor agents after further preclinical investigations.

Synthesis of 4-sulfamoylphenyl-benzylamine derivatives with inhibitory activity against human carbonic anhydrase isoforms I, II, IX and XII

Imine derivatives were obtained by condensation of sulfanilamide with substituted aromatic aldehydes. The Schiff bases were thereafter reduced with sodium borohydride, leading to the corresponding amines, derivatives of 4-sulfamoylphenyl-benzylamine. These sulfonamides were investigated as inhibitors of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I and II (cytosolic isozymes), as well as hCA IX and XII (transmembrane, tumor-associated enzymes). We noted that the compounds incorporating secondary amine moieties showed a better inhibitory activity against all CA isozymes compared to the corresponding Schiff bases. Low nanomolar CA II, IX and XII inhibitors were detected, whereas the activity against hCA I was less potent. The secondary amines incorporating sulfonamide or similar zinc-binding groups, poorly investigated chemotypes for designing metalloenzyme inhibitors, may offer interesting opportunities in the field due to the facile preparation and possibility to explore a vast chemical space.

Design, synthesis, evaluation and 3D-QSAR analysis of benzosulfonamide benzenesulfonates as potent and selective inhibitors of MMP-2

A novel series of MMPIs was designed, synthesized and purified using a scaffold modification strategy. The new compounds were also evaluated for biological activity against A549, MCF-7, HepG2 and Hela as potential inhibitors of MMP-2. The most potent inhi

Design, synthesis, molecular modeling, and biological evaluation of sulfanilamide-imines derivatives as potential anticancer agents

A series of sulfanilamide Schiff base derivatives (1 to 15) have been designed as potential antitubulin agents depending on the chemical structures of combretastatine A-4 and isoquinoline sulfamate (antimitotic agents under investigation). The designed co

Synthesis, antioxidant and antibacterial activities of some Schiff bases containing hydroxyl and methoxy groups

A series of Schiff bases were synthesized from different aromatic amines and aromatic aldehydes containing hydroxyl and methoxy groups. These compounds were characterized by IR and 1H NMR. All the compounds were screened for in vitro antioxidant activity using DPPH method and total reducing power activity based on the ability of compounds to reduce the Fe3+-TPTZ complex to the Fe2+/ferrous. Compounds substituted with hydroxyl and other electron donating groups, such as, methoxy groups showed low to high antioxidant activity. In addition, the compounds have been screened for their antibacterial activity against strains of Escherichia coli, Methycillinresistant Staphylococcus aureus, Klebsiella pneumonia and Pseudomonas aeruginosa. The tested Schiff bases at 5 mg/disc showed different antibacterial activities depending on the type of the tested bacterial species. However, E. coli appeared to be sensitive to seven compounds (Ia, Ib, Ic, Id, If, IIb and IIe), while methicillin resistant Staphylococcus aureus (MRSA) was affected by Ic, Ie, IIc and IIe compound. On the other hand, the compounds Ia, Ic, Id, Ie and IIh revealed antibacterial activity against Klebsiella spp. The Pseudomonas aeruginosa was not sensitive to any of the tested Schiff bases.

Microwave-assisted, solvent-free, parallel syntheses and elucidation of reaction mechanism for the formation of some novel tetraaryl imidazoles of biological interest

The microwave assisted, solvent free, parallel syntheses of title compounds is described in this protocol. Twelve new tetraaryl imidazoles, which are incorporated with the chemotherapeutic pharmaco- phores, have been synthesized by adopting one pot multic

Synthesis and study of antibacterial activity of some Schiff bases derived from sulfonamide, 4-amino antipyrene and raceacetophenone

Schiff bases derived from sulfonamide, 4-amino antipyrene and raceacetophenone were screened for antibacterial activity against various clinical isolates (obtained from Urine, Blood, Tracheal secretion and Pus). Extracts of these compounds were evaluated on 5 pathogenic strains [E. coli, Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella pneumoniae and Staphylococcus aureus]. The antibacterial activity was evaluated using the Agar Ditch method. The Schiff bases produced were (1) 4-[2-aza-2- (2-chlorophenyl) vinyl] benzene sulfonamide [AD1] (2) 4-[2-aza-2- (2-hydroxyphenyl) vinyl] benzene sulfonamide [AD2] (3) [1-aza-4-phenylbuta-1, 3-dienyl] benzene sulfonamide [AD3] (4) 4-[1-aza-2- (2chlorophenyl) vinyl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS1] (5) 4-[1-aza-2-(2-hydroxyphenyl) vinyl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS2] (6) 4-[1-aza-4-phenylbuta-1, 3-dienyl] 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS3] (7) 4-[2-aza-1-methyl-2- (2-nitro phenyl) vinyl]-6-ethylbenzene-1, 3-diol [ADS1] (8) 4-[2-aza-2(5-ehtyl-2, 4-dihydroxyphenyl) prop-1-enyl] benzene sulfonamide [ADS2]. The anti bacterial activity of these Schiff bases, were evaluated in one polar and one non polar (i.e., DMF and 1,4 dioxan) solvents. It is found that among AD and AS compounds AD compounds are better than AS and AD3 is the best while 1,4 dioxan solvent proved to be more effective than DMF. It appears that the sulfonamide moiety present with cinnamaldehyde side chain could be used as a lead molecule in drug designing (i.e. in inhibiting the above pathogenic bacteria).

Carbonic anhydrase inhibitors. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: The first inhibitors with equally high affinity towards cytosolic and membrane-bound isozymes

A series of Schiff bases was prepared by reaction of sulfanilamide with substituted benzene- and heterocyclic aldehydes. The compounds were characterized by standard procedures, and were assayed as inhibitors of the zinc enzyme carbonic anhydrase (CA). Th

Characterization and Formation Constants of La(III), Ce(III), Pr(III), Nd(III), Sm(III), Eu(III), Gd(III), Tb(III), Dy(III), Ho(III), Er(III), Tm(III), Yb(III) and Lu(III) Complexes of Schiff Base Derived from Sulphanilamide and Salicylaldehyde

A few lanthanide complexes of the type ML3*2H2O where LH is a schiff base derived from sulphanilamide and salicylaldehyde have been synthesized and characterized on the basis of their elemental analysis, infrared spectra and molar conductance measurements.The schiff base acts as a monobasic bidentate ligand and the complexes appear to be eight coordinated.The pH-metric studies have been carried out to determine the proton-ligand stability constants of the ligand and metal-ligand stability constants of its complexes at 25 deg C and 0.1 M ionic strength.The stability constants of these rare earth complexes follow the order: Ce > Dy > Pr > Lu > Tm > Eu > La > Yb > Er > Nd > Ho > Tb > Sm > Gd.