The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

SureCN729     benzenesulfonamide

Synonyms: CHEMBL27601, NSC-5341, AG-B-57106, ACMC-20978z, ANW-13665, ...
Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of benzenesulfonamide


Psychiatry related information on benzenesulfonamide


High impact information on benzenesulfonamide

  • The ionized NH(-) group of each benzenesulfonamide coordinates to the active site Zn(2+) ion; the IDA-Cu(2+) prong of the tightest-binding inhibitor, BR30, binds to H64 of CAII and H200 of CAI [6].
  • The experimental data revealed that whereas the binding affinity of L1 for hCA-I was similar to that of benzenesulfonamide, the binding affinity of L2 was approximately 2 orders of magnitude higher, making L2 one of the most potent ligands or inhibitors of hCA-I [7].
  • Synthesis and cyclooxygenase-2 inhibiting property of 1,5-diarylpyrazoles with substituted benzenesulfonamide moiety as pharmacophore: Preparation of sodium salt for injectable formulation [8].
  • A series of 1,5-diarylpyrazoles having a substituted benzenesulfonamide moiety as pharmacophore was synthesized and evaluated for cyclooxygenase (COX-1/COX-2) inhibitory activities [8].
  • In solution, the benzenesulfonamide group coordinates as an anion to a Zn(II) ion bound at the active site of the enzyme [9].

Biological context of benzenesulfonamide


Associations of benzenesulfonamide with other chemical compounds


Gene context of benzenesulfonamide

  • Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II [19].
  • Substitution at the ortho position of N-(3,4-dimethyl-5-isoxazolyl) benzenesulfonamide led to the identification of the biphenylsulfonamides as a novel series of endothelin-A (ETA) selective antagonists [20].
  • As part of an effort to further explore the function of 5-HT2C receptors, we have developed a selective 5-HT2C receptor antagonist, RS-102221 (a benzenesulfonamide of 8-[5-(5-amino-2,4-dimethoxyphenyl) 5-oxopentyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione) [21].
  • These results indicate a substituted benzenesulfonamide safener might be used with the promoters from the In2-1 and In2-2 genes to develop a new inducible gene expression system for plants [12].
  • By exploiting crystal structures of several complexes between CDK2 and inhibitors and applying structure-based drug design (SBDD), we rapidly discovered a very potent and selective CDK2 inhibitor 4-[(5-isopropyl-1,3-thiazol-2-yl)amino] benzenesulfonamide (compound 4, IC(50)=20nM) [22].

Analytical, diagnostic and therapeutic context of benzenesulfonamide


  1. Short communication inhibitory activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene)amino]-N-(4,6-dimethylpyrimidin-2-yl) benzenesulphonamide and its derivatives against orthopoxvirus replication in vitro. Selvam, P., Murugesh, N., Chandramohan, M., Keith, K.A., Kern, E.R. Antivir. Chem. Chemother. (2006) [Pubmed]
  2. A celecoxib derivative potently inhibits proliferation of colon adenocarcinoma cells by induction of apoptosis. Kusunoki, N., Ito, T., Sakurai, N., Handa, H., Kawai, S. Anticancer Res. (2006) [Pubmed]
  3. Valdecoxib-induced toxic epidermal necrolysis in a patient allergic to sulfa drugs. Glasser, D.L., Burroughs, S.H. Pharmacotherapy (2003) [Pubmed]
  4. PC-407 inhibited proliferation and induced apoptosis in human colon cancer SW-1116 cells. Hao, L.L., Mei, Q.B., Zhang, B.L., Jia, M., Li, X.Q., Zhang, F. Acta Pharmacol. Sin. (2004) [Pubmed]
  5. Evaluation of some benzenesulphonylhydrazones of aryl aldehydes and ketones as antiepileptic agents. Dimmock, J.R., Brenner, J.M., Phillips, O.A. Die Pharmazie. (1987) [Pubmed]
  6. Ultrahigh resolution crystal structures of human carbonic anhydrases I and II complexed with "two-prong" inhibitors reveal the molecular basis of high affinity. Jude, K.M., Banerjee, A.L., Haldar, M.K., Manokaran, S., Roy, B., Mallik, S., Srivastava, D.K., Christianson, D.W. J. Am. Chem. Soc. (2006) [Pubmed]
  7. Spacer-based selectivity in the binding of "two-prong" ligands to recombinant human carbonic anhydrase I. Banerjee, A.L., Eiler, D., Roy, B.C., Jia, X., Haldar, M.K., Mallik, S., Srivastava, D.K. Biochemistry (2005) [Pubmed]
  8. Synthesis and cyclooxygenase-2 inhibiting property of 1,5-diarylpyrazoles with substituted benzenesulfonamide moiety as pharmacophore: Preparation of sodium salt for injectable formulation. Pal, M., Madan, M., Padakanti, S., Pattabiraman, V.R., Kalleda, S., Vanguri, A., Mullangi, R., Mamidi, N.V., Casturi, S.R., Malde, A., Gopalakrishnan, B., Yeleswarapu, K.R. J. Med. Chem. (2003) [Pubmed]
  9. Probing the energetics of dissociation of carbonic anhydrase-ligand complexes in the gas phase. Gao, J., Wu, Q., Carbeck, J., Lei, Q.P., Smith, R.D., Whitesides, G.M. Biophys. J. (1999) [Pubmed]
  10. Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high-affinity inhibitors of kynurenine 3-hydroxylase. Röver, S., Cesura, A.M., Huguenin, P., Kettler, R., Szente, A. J. Med. Chem. (1997) [Pubmed]
  11. Molecular structure and conformations of benzenesulfonamide: gas electron diffraction and quantum chemical calculations. Petrov, V., Petrova, V., Girichev, G.V., Oberhammer, H., Giricheva, N.I., Ivanov, S. J. Org. Chem. (2006) [Pubmed]
  12. Isolation and characterization of cDNA clones for RNA species induced by substituted benzenesulfonamides in corn. Hershey, H.P., Stoner, T.D. Plant Mol. Biol. (1991) [Pubmed]
  13. Subtle differences in dissociation rates of interactions between destabilized human carbonic anhydrase II mutants and immobilized benzenesulfonamide inhibitors probed by a surface plasmon resonance biosensor. Svedhem, S., Enander, K., Karlsson, M., Sjöbom, H., Liedberg, B., Löfås, S., Mårtensson, L.G., Sjöstrand, S.E., Svensson, S., Carlsson, U., Lundström, I. Anal. Biochem. (2001) [Pubmed]
  14. QSAR study on benzenesulphonamide carbonic anhydrase inhibitors: topological approach using Balaban index. Thakur, A., Thakur, M., Khadikar, P.V., Supuran, C.T., Sudele, P. Bioorg. Med. Chem. (2004) [Pubmed]
  15. Protein surface-assisted enhancement in the binding affinity of an inhibitor for recombinant human carbonic anhydrase-II. Banerjee, A.L., Swanson, M., Roy, B.C., Jia, X., Haldar, M.K., Mallik, S., Srivastava, D.K. J. Am. Chem. Soc. (2004) [Pubmed]
  16. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. Talley, J.J., Brown, D.L., Carter, J.S., Graneto, M.J., Koboldt, C.M., Masferrer, J.L., Perkins, W.E., Rogers, R.S., Shaffer, A.F., Zhang, Y.Y., Zweifel, B.S., Seibert, K. J. Med. Chem. (2000) [Pubmed]
  17. Nitrogen-15 nuclear magnetic resonance study of benzenesulfonamide and cyanate binding to carbonic anhydrase. Kanamori, K., Roberts, J.D. Biochemistry (1983) [Pubmed]
  18. Potent, selective 3-pyridylethanolamine beta3 adrenergic receptor agonists possessing a thiazole benzenesulfonamide pharmacophore. Mathvink, R.J., Tolman, J.S., Chitty, D., Candelore, M.R., Cascieri, M.A., Colwell, L.F., Deng, L., Feeney, W.P., Forrest, M.J., Hom, G.J., MacIntyre, D.E., Tota, L., Wyvratt, M.J., Fisher, M.H., Weber, A.E. Bioorg. Med. Chem. Lett. (2000) [Pubmed]
  19. Carbonic anhydrase inhibitors: X-ray crystal structure of a benzenesulfonamide strong CA II and CA IX inhibitor bearing a pentafluorophenylaminothioureido tail in complex with isozyme II. Di Fiore, A., De Simone, G., Menchise, V., Pedone, C., Casini, A., Scozzafava, A., Supuran, C.T. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  20. Biphenylsulfonamide endothelin antagonists: structure-activity relationships of a series of mono- and disubstituted analogues and pharmacology of the orally active endothelin antagonist 2'-amino-N- (3,4-dimethyl-5-isoxazolyl)-4'-(2-methylpropyl)[1, 1'-biphenyl]-2-sulfonamide (BMS-187308). Murugesan, N., Gu, Z., Stein, P.D., Bisaha, S., Spergel, S., Girotra, R., Lee, V.G., Lloyd, J., Misra, R.N., Schmidt, J., Mathur, A., Stratton, L., Kelly, Y.F., Bird, E., Waldron, T., Liu, E.C., Zhang, R., Lee, H., Serafino, R., Abboa-Offei, B., Mathers, P., Giancarli, M., Seymour, A.A., Webb, M.L., Hunt, J.T. J. Med. Chem. (1998) [Pubmed]
  21. RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist. Bonhaus, D.W., Weinhardt, K.K., Taylor, M., DeSouza, A., McNeeley, P.M., Szczepanski, K., Fontana, D.J., Trinh, J., Rocha, C.L., Dawson, M.W., Flippin, L.A., Eglen, R.M. Neuropharmacology (1997) [Pubmed]
  22. Structure-based drug design to the discovery of new 2-aminothiazole CDK2 inhibitors. Vulpetti, A., Casale, E., Roletto, F., Amici, R., Villa, M., Pevarello, P. J. Mol. Graph. Model. (2006) [Pubmed]
WikiGenes - Universities