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Research Article

Carbonic Anhydrase Inhibitors: Synthesis of Water Soluble Sulfonamides Incorporating a 4-sulfamoylphenylmethylthiourea Scaffold, with Potent Intraocular Pressure Lowering Properties

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Pages 333-343 | Published online: 30 Sep 2008

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Read on this site (10)

Yosselin Huentupil, Luis Peña, Néstor Novoa, Emanuela Berrino, Rodrigo Arancibia & Claudiu T. Supuran. (2019) New sulfonamides containing organometallic-acylhydrazones: synthesis, characterisation and biological evaluation as inhibitors of human carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 34:1, pages 451-458.
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Ramazan Demirdag, Emrah Yerlikaya & Omer Irfan Kufrevioglu. (2012) Purification of carbonic anhydrase-II from sheep liver and inhibitory effects of some heavy metals on enzyme activity. Journal of Enzyme Inhibition and Medicinal Chemistry 27:6, pages 795-799.
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Özen Özensoy, Mikail Arslan & Claudiu T. Supuran. (2011) Carbonic anhydrase inhibitors: purification and inhibition studies of pigeon (Columba livia var. domestica) red blood cell carbonic anhydrase with sulfonamides. Journal of Enzyme Inhibition and Medicinal Chemistry 26:5, pages 749-753.
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Deniz Ekİncİ, Şükrü Beydemir & Ö. İrfan Küfrevİoğlu. (2007) In vitro inhibitory effects of some heavy metals on human erythrocyte carbonic anhydrases. Journal of Enzyme Inhibition and Medicinal Chemistry 22:6, pages 745-750.
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Yaşar Demİr, Hayrunnisa Nadaroğlu & Nazan Demİr. (2005) Purification and characterization of carbonic anhydrase from bovine stomach and effects of some known inhibitors on enzyme activity. Journal of Enzyme Inhibition and Medicinal Chemistry 20:1, pages 75-80.
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Özen Özensoy, Semra Isik, Oktay Arslan, Mikail Arslan, Andrea Scozzafava & Claudiu T. Supuran. (2005) Carbonic anhydrase inhibitors. Inhibition of red blood cell ostrich (Struthio camelus) carbonic anhydrase with a series of aromatic and heterocyclic sulfonamides. Journal of Enzyme Inhibition and Medicinal Chemistry 20:4, pages 383-387.
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Andrea Scozzafava, Antonio Mastrolorenzo & Claudiu T Supuran. (2004) Modulation of carbonic anhydrase activity and its applications in therapy. Expert Opinion on Therapeutic Patents 14:5, pages 667-702.
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Metin BÜLBÜL, Olcay HİSAR, Şükrü BEYDEMİR, Mehmet ÇİFTÇİ & Ö. İrfan KÜFREVIOĞLU. (2003) The In Vitro and In Vivo Inhibitory Effects of Some Sulfonamide Derivatives on Rainbow Trout (Oncorhynchus Mykiss) Erythrocyte Carbonic Anhydrase Activity. Journal of Enzyme Inhibition and Medicinal Chemistry 18:4, pages 371-375.
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Francesco Abbate, Angela Casini, Andrea Scozzafava & Claudiu T. Supuran. (2003) Carbonic Anhydrase Inhibitors: X-ray Crystallographic Structure of the Adduct of Human Isozyme II with the Perfluorobenzoyl Analogue of Methazolamide. Implications for the Drug Design of Fluorinated Inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 18:4, pages 303-308.
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Articles from other publishers (23)

Pınar Eraslan‐Elma, Atilla Akdemir, Emanuela Berrino, Murat Bozdağ, Claudiu T. Supuran & Nilgün Karalı. (2022) New 1 H ‐indole‐2,3‐dione 3‐thiosemicarbazones with 3‐sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors . Archiv der Pharmazie 355:8.
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Soumajit Ghorai, Sravani Pulya, Kalyan Ghosh, Parthasarathi Panda, Balaram Ghosh & Shovanlal Gayen. (2020) Structure-activity relationship of human carbonic anhydrase-II inhibitors: Detailed insight for future development as anti-glaucoma agents. Bioorganic Chemistry 95, pages 103557.
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Nabih Lolak, Suleyman Akocak, Silvia Bua, Rajesh K.K. Sanku & Claudiu T. Supuran. (2019) Discovery of new ureido benzenesulfonamides incorporating 1,3,5-triazine moieties as carbonic anhydrase I, II, IX and XII inhibitors. Bioorganic & Medicinal Chemistry 27:8, pages 1588-1594.
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Nabih Lolak, Suleyman Akocak, Silvia Bua & Claudiu T. Supuran. (2019) Design, synthesis and biological evaluation of novel ureido benzenesulfonamides incorporating 1,3,5-triazine moieties as potent carbonic anhydrase IX inhibitors. Bioorganic Chemistry 82, pages 117-122.
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Niccolò Chiaramonte, Maria Romanelli, Elisabetta Teodori & Claudiu Supuran. (2018) Amino Acids as Building Blocks for Carbonic Anhydrase Inhibitors. Metabolites 8:2, pages 36.
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Nabih Lolak, Suleyman Akocak, Silvia Bua, Murat Koca & Claudiu T. Supuran. (2018) Design and synthesis of novel 1,3-diaryltriazene-substituted sulfonamides as potent and selective carbonic anhydrase II inhibitors. Bioorganic Chemistry 77, pages 542-547.
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Suleyman Akocak, Nabih Lolak, Silvia Bua, Idris Turel & Claudiu T. Supuran. (2018) Synthesis and biological evaluation of novel N,N′-diaryl cyanoguanidines acting as potent and selective carbonic anhydrase II inhibitors. Bioorganic Chemistry 77, pages 245-251.
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Murat Bozdag, Ahmed Mahmoud Alafeefy, Abdul Malik Altamimi, Fabrizio Carta, Claudiu T. Supuran & Daniela Vullo. (2017) Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII. Bioorganic & Medicinal Chemistry 25:10, pages 2782-2788.
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Vincenzo Alterio, Anna Di Fiore, Katia D’Ambrosio, Claudiu T. Supuran & Giuseppina De Simone. (2012) Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms?. Chemical Reviews 112:8, pages 4421-4468.
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Janina Moeker, Kanae Teruya, Sabine Rossit, Brendan L. Wilkinson, Marie Lopez, Laurent F. Bornaghi, Alessio Innocenti, Claudiu T. Supuran & Sally-Ann Poulsen. (2012) Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases. Bioorganic & Medicinal Chemistry 20:7, pages 2392-2404.
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R. E. Masto, L. C. Ram, P. R. Shandilya, S. Sinha, J. George & V. A. Selvi. (2011) Selection of bioindicators in coal-contaminated soils of Dhanbad, India. Environmental Earth Sciences 64:4, pages 1107-1115.
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Vincenzo Alterio, Anna Di Fiore, Katia D'Ambrosio, Claudiu T. Supuran & Giuseppina De Simone. 2009. Drug Design of Zinc‐Enzyme Inhibitors. Drug Design of Zinc‐Enzyme Inhibitors 138 66 .
Marouan Rami, Alessandro Cecchi, Jean-Louis Montero, Alessio Innocenti, Daniela Vullo, Andrea Scozzafava, Jean-Yves Winum & Claudiu T. Supuran. (2008) Carbonic Anhydrase Inhibitors: Design of Membrane-Impermeant Copper(II) Complexes of DTPA-, DOTA-, and TETA-Tailed Sulfonamides Targeting the Tumor-Associated Transmembrane Isoform IX. ChemMedChem 3:11, pages 1780-1788.
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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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Georgia Melagraki, Antreas Afantitis, Haralambos Sarimveis, Olga Igglessi-Markopoulou & Claudiu T. Supuran. (2006) QSAR study on para-substituted aromatic sulfonamides as carbonic anhydrase II inhibitors using topological information indices. Bioorganic & Medicinal Chemistry 14:4, pages 1108-1114.
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Jerzy Zakrzewski & Maria Krawczyk. (2006) Reactions of nitroxides with sulfur-containing compounds, part IV: Synthesis of novel nitroxide (thio)ureas. Heteroatom Chemistry 17:5, pages 393-401.
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Özen Özensoy, Luca Puccetti, Giuseppe Fasolis, Oktay Arslan, Andrea Scozzafava & Claudiu T. Supuran. (2005) Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides. Bioorganic & Medicinal Chemistry Letters 15:21, pages 4862-4866.
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Özen Özensoy, Isao Nishimori, Daniela Vullo, Luca Puccetti, Andrea Scozzafava & Claudiu T. Supuran. (2005) Carbonic anhydrase inhibitors: Inhibition of the human transmembrane isozyme XIV with a library of aromatic/heterocyclic sulfonamides. Bioorganic & Medicinal Chemistry 13:22, pages 6089-6093.
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Francesco Mincione, Michele Starnotti, Emanuela Masini, Lucia Bacciottini, Chiara Scrivanti, Angela Casini, Daniela Vullo, Andrea Scozzafava & Claudiu T. Supuran. (2005) Carbonic anhydrase inhibitors: Design of thioureido sulfonamides with potent isozyme II and XII inhibitory properties and intraocular pressure lowering activity in a rabbit model of glaucoma. Bioorganic & Medicinal Chemistry Letters 15:17, pages 3821-3827.
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Luca Puccetti, Giuseppe Fasolis, Alessandro Cecchi, Jean-Yves Winum, Alessandro Gamberi, Jean-Louis Montero, Andrea Scozzafava & Claudiu T. Supuran. (2005) Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporating thioureido-sulfanilyl scaffolds. Bioorganic & Medicinal Chemistry Letters 15:9, pages 2359-2364.
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Anna Di Fiore, Giuseppina De Simone, Valeria Menchise, Carlo Pedone, Angela Casini, Andrea Scozzafava & Claudiu T. Supuran. (2005) 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. Bioorganic & Medicinal Chemistry Letters 15:7, pages 1937-1942.
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Alessandro Cecchi, Jean-Yves Winum, Alessio Innocenti, Daniela Vullo, Jean-Louis Montero, Andrea Scozzafava & Claudiu T. Supuran. (2004) Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide. Bioorganic & Medicinal Chemistry Letters 14:23, pages 5775-5780.
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Angela Casini, Francesco Abbate, Andrea Scozzafava & Claudiu T Supuran. (2003) Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a bis-sulfonamide—two heads are better than one?. Bioorganic & Medicinal Chemistry Letters 13:16, pages 2759-2763.
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