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Original Article

Carbonic Anhydrase Inhibitors. Arylsulfonylureido-and Arylureido-Substituted Aromatic and Heterocyclic Sulfonamides: Towards Selective Inhibitors of Carbonic Anhydrase Isozyme I

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Pages 343-363 | Received 29 Oct 1998, Published online: 02 Jul 2009

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Read on this site (19)

Maristela Barbosa Portela, Caroliny Mello Barboza, Eduardo Moreira da Silva, Daniel Clemente de Moraes, Renata Antoun Simão, Clara Ribeiro de Souza, Verônica da Silva Cardoso, Antônio Ferreira-Pereira, Alane Beatriz Vermelho & Claudiu T. Supuran. (2023) Dentine biomodification by sulphonamides pre-treatment: bond strength, proteolytic inhibition, and antimicrobial activity. Journal of Enzyme Inhibition and Medicinal Chemistry 38:1, pages 319-329.
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Yakup Budak, Umit M. Kocyigit, Meliha Burcu Gürdere, Kezban Özcan, Parham Taslimi, İlhami Gülçin & Mustafa Ceylan. (2017) Synthesis and investigation of antibacterial activities and carbonic anhydrase and acetyl cholinesterase inhibition profiles of novel 4,5-dihydropyrazol and pyrazolyl-thiazole derivatives containing methanoisoindol-1,3-dion unit. Synthetic Communications 47:24, pages 2313-2323.
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Belma Zengin Kurt, Fatih Sonmez, Serdar Durdagi, Busecan Aksoydan, Ramin Ekhteiari Salmas, Andrea Angeli, Mustafa Kucukislamoglu & Claudiu T. Supuran. (2017) Synthesis, biological activity and multiscale molecular modeling studies for coumaryl-carboxamide derivatives as selective carbonic anhydrase IX inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 1042-1052.
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Erol Licsandru, Muhammet Tanc, Istvan Kocsis, Mihail Barboiu & Claudiu T. Supuran. (2017) A class of carbonic anhydrase I – selective activators. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 37-46.
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Belma Zengin Kurt, Fatih Sönmez, Çiğdem Bilen, Adem Ergun, Nahit Gençer, Oktay Arslan & Mustafa Kucukislamoglu. (2016) Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 991-998.
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Claudiu T. Supuran. (2016) How many carbonic anhydrase inhibition mechanisms exist?. Journal of Enzyme Inhibition and Medicinal Chemistry 31:3, pages 345-360.
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Erik O. Pettersen, Peter Ebbesen, Roben G. Gieling, Kaye J. Williams, Ludwig Dubois, Philippe Lambin, Carol Ward, James Meehan, Ian H. Kunkler, Simon P. Langdon, Anne H. Ree, Kjersti Flatmark, Heidi Lyng, Maria J. Calzada, Luis del Peso, Manuel O. Landazuri, Agnes Görlach, Hubert Flamm, Jochen Kieninger, Gerald Urban, Andreas Weltin, Dean C. Singleton, Syed Haider, Francesca M. Buffa, Adrian L. Harris, Andrea Scozzafava, Claudiu T. Supuran, Isabella Moser, Gerhard Jobst, Morten Busk, Kasper Toustrup, Jens Overgaard, Jan Alsner, Jacques Pouyssegur, Johanna Chiche, Nathalie Mazure, Ibtissam Marchiq, Scott Parks, Afshan Ahmed, Margaret Ashcroft, Silvia Pastorekova, Yihai Cao, Kasper M. Rouschop, Brad G. Wouters, Marianne Koritzinsky, Hilda Mujcic & Dan Cojocari. (2015) Targeting tumour hypoxia to prevent cancer metastasis. From biology, biosensing and technology to drug development: the METOXIA consortium. Journal of Enzyme Inhibition and Medicinal Chemistry 30:5, pages 689-721.
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Giuseppina De Simone, Vincenzo Alterio & Claudiu T Supuran. (2013) Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opinion on Drug Discovery 8:7, pages 793-810.
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Claudiu T. Supuran. (2012) Structure-based drug discovery of carbonic anhydrase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 27:6, pages 759-772.
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Tholappanavara H. Suresha Kumara, KittappaM. Mahadevan, HosanagaraN. Harishkumar, Basavaraj Padmashali & Gadada Naganagowda. (2009) Synthesis of Benzo[b]thiophene Substituted Carbamates, Ureas, Semicarbazides, and Pyrazoles and Their Antimicrobial and Analgesic Activity. Phosphorus, Sulfur, and Silicon and the Related Elements 184:7, pages 1866-1879.
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Andrea Scozzafava, Antonio Mastrolorenzo & Claudiu T. Supuran. (2001) Antimycobacterial Activity of 3,4-dichlorophenyl-ureas, N,N-diphenyl-ureas and Related Derivatives. Journal of Enzyme Inhibition 16:5, pages 425-432.
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Brian W. Clare, Andrea Scozzafava & Claudiu T. Supuran. (2001) Protease Inhibitors, Part 13: Specific, Weakly Basic Thrombin Inhibitors Incorporating Sulfonyl Dicyandiamide Moieties in their Structure. Journal of Enzyme Inhibition 16:1, pages 1-13.
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Claudiu T. Supuran & Andrea Scozzafava. (2000) Carbonic Anhydrase Inhibitors: Aromatic Sulfonamides and Disulfonamides Act as Efficient Tumor Growth Inhibitors. Journal of Enzyme Inhibition 15:6, pages 597-610.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T. Supuran. (2000) The Antifungal Activity of Sulfonylated/Carboxylated Derivatives of Dibenzo-1,4-Dioxine-2-Acetyloxime May Be Due to Inhibition of Lanosterol-14Al-Demethylase. Journal of Enzyme Inhibition 15:6, pages 557-569.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T. Supuran. (2000) Antifungal Activity of Ag(I) and Zn(Ii) Complexes of Aminobenzolamide (5-Sulfanilylamido-1,3,4-Thiadiazole-2-Sulfonamide) Derivatives. Journal of Enzyme Inhibition 15:6, pages 517-531.
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Andrea Scozzafava, Mircea D. Banciu, Angela Popescu & Claudiu T. Supuran. (2000) Carbonic Anhydrase Inhibitors: Inhibition of Isozymes I, II and IV by Sulfamide and Sulfamic Acid Derivatives. Journal of Enzyme Inhibition 15:5, pages 443-453.
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Brian W. Clare, Andrea Scozzafava, Fabrizio Briganti, Bogdan Iorga & Claudiu T. Supuran. (2000) Protease Inhibitors. Part 2. Weakly Basic Thrombin Inhibitors Incorporating Sulfonyl-Aminoguanidine Moieties as S1 Anchoring Groups: Synthesis and Structure-Activity Correlations. Journal of Enzyme Inhibition 15:3, pages 235-264.
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Claudiu T. Supuran, Fabrizio Briganti, Giovanna Mincione & Andrea Scozzafava. (2000) Protease Inhibitors: Synthesis of L-Alanine Hydroxamate Sulfonylated Derivatives as Inhibitors of Clostridium Histolyticum Collagenase. Journal of Enzyme Inhibition 15:2, pages 111-128.
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Articles from other publishers (29)

Srinivas Angapelly, P.V. Sri Ramya, Andrea Angeli, Simona Maria Monti, Martina Buonanno, Mallika Alvala, Cladiu T. Supuran & Mohammed Arifuddin. (2017) Discovery of 4-sulfamoyl-phenyl-β-lactams as a new class of potent carbonic anhydrase isoforms I, II, IV and VII inhibitors: The first example of subnanomolar CA IV inhibitors. Bioorganic & Medicinal Chemistry 25:2, pages 539-544.
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Marta Ferraroni, Fabrizio Carta, Andrea Scozzafava & Claudiu T. Supuran. (2015) Thioxocoumarins Show an Alternative Carbonic Anhydrase Inhibition Mechanism Compared to Coumarins. Journal of Medicinal Chemistry 59:1, pages 462-473.
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Marco Bragagni, Murat Bozdag, Fabrizio Carta, Andrea Scozzafava, Cecilia Lanzi, Emanuela Masini, Paola Mura & Claudiu T. Supuran. (2015) Cyclodextrin complexation highly enhances efficacy of arylsulfonylureido benzenesulfonamide carbonic anhydrase inhibitors as a topical antiglaucoma agents. Bioorganic & Medicinal Chemistry 23:18, pages 6223-6227.
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Mariangela Ceruso, Sabrina Antel, Daniela Vullo, Andrea Scozzafava & Claudiu T. Supuran. (2014) Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I–XIV. Bioorganic & Medicinal Chemistry 22:24, pages 6768-6775.
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Murat Bozdag, Marta Ferraroni, Fabrizio Carta, Daniela Vullo, Laura Lucarini, Elisabetta Orlandini, Armando Rossello, Elisa Nuti, Andrea Scozzafava, Emanuela Masini & Claudiu T. Supuran. (2014) Structural Insights on Carbonic Anhydrase Inhibitory Action, Isoform Selectivity, and Potency of Sulfonamides and Coumarins Incorporating Arylsulfonylureido Groups. Journal of Medicinal Chemistry 57:21, pages 9152-9167.
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Jayashree Pichake, Prashant S. Kharkar, Mariangela Ceruso, Claudiu T. Supuran & Mrunmayee P. Toraskar. (2014) Carbonic Anhydrase Inhibitors: Design, Synthesis, and Biological Evaluation of Novel Sulfonyl Semicarbazide Derivatives. ACS Medicinal Chemistry Letters 5:7, pages 793-796.
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Robert McKenna & Claudiu T. Supuran. 2014. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications. Carbonic Anhydrase: Mechanism, Regulation, Links to Disease, and Industrial Applications 291 323 .
Alaa A.-M. Abdel-Aziz, Adel S. El-Azab, Hussein I. El-Subbagh, Abdulrahman M. Al-Obaid, Amer M. Alanazi & Mohamed A. Al-Omar. (2012) Design, synthesis, single-crystal and preliminary antitumor activity of novel arenesulfonylimidazolidin-2-ones. Bioorganic & Medicinal Chemistry Letters 22:5, pages 2008-2014.
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Fabio Pacchiano, Fabrizio Carta, Paul C. McDonald, Yuanmei Lou, Daniela Vullo, Andrea Scozzafava, Shoukat Dedhar & Claudiu T. Supuran. (2011) Ureido-Substituted Benzenesulfonamides Potently Inhibit Carbonic Anhydrase IX and Show Antimetastatic Activity in a Model of Breast Cancer Metastasis. Journal of Medicinal Chemistry 54:6, pages 1896-1902.
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Fabio Pacchiano, Fabrizio Carta, Daniela Vullo, Andrea Scozzafava & Claudiu T. Supuran. (2011) Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides. Bioorganic & Medicinal Chemistry Letters 21:1, pages 102-105.
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Ibrahim M. El-Deeb, Said M. Bayoumi, Magda A. El-Sherbeny & Alaa A.-M. Abdel-Aziz. (2010) Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction. European Journal of Medicinal Chemistry 45:6, pages 2516-2530.
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Claudiu T. Supuran & Jean‐Yves Winum. 2009. Drug Design of Zinc‐Enzyme Inhibitors. Drug Design of Zinc‐Enzyme Inhibitors 399 413 .
Mohamed S. Al‐Saadi, Sherif. A. F. Rostom & Hassan M. Faidallah. (2008) 3‐Methyl‐2‐(4‐substituted phenyl)‐4,5‐dihydronaphtho[1,2‐ c ]‐pyrazoles: Synthesis and in‐vitro Biological Evaluation as Antitumour Agents . Archiv der Pharmazie 341:3, pages 181-190.
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Claudiu T. Supuran & Andrea Scozzafava. (2007) Carbonic anhydrases as targets for medicinal chemistry. Bioorganic & Medicinal Chemistry 15:13, pages 4336-4350.
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Sherif A.F. Rostom. (2006) Synthesis and in vitro antitumor evaluation of some indeno[1,2-c]pyrazol(in)es substituted with sulfonamide, sulfonylurea(-thiourea) pharmacophores, and some derived thiazole ring systems. Bioorganic & Medicinal Chemistry 14:19, pages 6475-6485.
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Alexander Hillebrecht, Claudiu T. Supuran & Gerhard Klebe. (2006) Integrated Approach Using Protein and Ligand Information to Analyze Selectivity- and Affinity-Determining Features of Carbonic Anhydrase Isozymes. ChemMedChem 1:8, pages 839-853.
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P. R. Latthe, P. S. Shinge, Bharati V. Badami, P. B. Patil & S. N. Holihosur. (2006) Curtius rearrangement reactions of 3-(4-azidocarbonyl) phenylsydnone. Synthesis of 4-(sydnon-3-yl) phenyl carbamates, N-aryl-N′-[4-(sydnon-3-yl)] phenyl ureas and their antimicrobial and insecticidal activities. Journal of Chemical Sciences 118:3, pages 249-256.
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Marc A Ilies, Bernard Masereel, Stéphanie Rolin, Andrea Scozzafava, Gheorghe Câmpeanu, Valentin Cı̂mpeanu & Claudiu T Supuran. (2004) Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. Bioorganic & Medicinal Chemistry 12:10, pages 2717-2726.
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Claudiu T. Supuran, Andrea Scozzafava & Angela Casini. (2002) Carbonic anhydrase inhibitors. Medicinal Research Reviews 23:2, pages 146-189.
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Claudiu T Supuran, Fabrizio Briganti, Silvia Tilli, W.Richard Chegwidden & Andrea Scozzafava. (2001) Carbonic anhydrase inhibitors: Sulfonamides as antitumor agents?. Bioorganic & Medicinal Chemistry 9:3, pages 703-714.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T. Supuran. (2000) 4-Toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents. European Journal of Pharmaceutical Sciences 11:4, pages 325-332.
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Antonio Mastrolorenzo, Andrea Scozzafava & Claudiu T Supuran. (2000) Antifungal activity of silver and zinc complexes of sulfadrug derivatives incorporating arylsulfonylureido moieties. European Journal of Pharmaceutical Sciences 11:2, pages 99-107.
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Andrea Scozzafava, Marc A Ilies, Gheorghe Manole & Claudiu T Supuran. (2000) Protease inhibitors. European Journal of Pharmaceutical Sciences 11:1, pages 69-79.
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Andrea Scozzafava & Claudiu T. Supuran. (2000) Carbonic anhydrase inhibitors: synthesis of N -morpholyl-thiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV. Bioorganic & Medicinal Chemistry Letters 10:10, pages 1117-1120.
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Andrea Scozzafava & Claudiu T. Supuran. (2000) Protease inhibitors. Part 8: synthesis of potent Clostridium histolyticum collagenase inhibitors incorporating sulfonylated l -alanine hydroxamate moieties. Bioorganic & Medicinal Chemistry 8:3, pages 637-645.
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Andrea Scozzafava & Claudiu T Supuran. (2000) Protease inhibitors: synthesis of Clostridium histolyticum collagenase inhibitors incorporating sulfonyl-l-alanine hydroxamate moieties. Bioorganic & Medicinal Chemistry Letters 10:5, pages 499-502.
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Claudiu T Supuran & Andrea Scozzafava. (2000) Protease inhibitors. Part 7. European Journal of Pharmaceutical Sciences 10:1, pages 67-76.
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Andrea Scozzafava & Claudiu T. Supuran. (2000) Carbonic anhydrase activators. European Journal of Pharmaceutical Sciences 10:1, pages 29-41.
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A Scozzafava. (2000) Protease inhibitors – Part 5. Alkyl/arylsulfonyl- and arylsulfonylureido-/arylureido- glycine hydroxamate inhibitors of Clostridium histolyticum collagenase. European Journal of Medicinal Chemistry 35:3, pages 299-307.
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