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Research Article

Fluorinated pyrrolidines and piperidines incorporating tertiary benzenesulfonamide moieties are selective carbonic anhydrase II inhibitors

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Pages 737-745 | Received 26 Aug 2014, Accepted 03 Sep 2014, Published online: 28 Nov 2014

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Claudiu T. Supuran. (2020) Exploring the multiple binding modes of inhibitors to carbonic anhydrases for novel drug discovery. Expert Opinion on Drug Discovery 15:6, pages 671-686.
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Alessio Nocentini & Claudiu T. Supuran. (2019) Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opinion on Drug Discovery 14:11, pages 1175-1197.
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Ekaterina A. Anikina, Andrey V. Smolobochkin, Almir S. Gazizov, Alexander R. Burilov & Michail A. Pudovik. (2018) Synthesis of 1-sulfonyl-2-arylpyrrolidines via intramolecular cyclization/Mannich-type reaction cascade of N-(4,4-diethoxybutyl)sulfonamides. Phosphorus, Sulfur, and Silicon and the Related Elements 193:11, pages 766-770.
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Claudiu T. Supuran. (2017) Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opinion on Drug Discovery 12:1, pages 61-88.
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Emir Alper Türkoğlu, Murat Şentürk, Claudiu T. Supuran & Deniz Ekinci. (2017) Carbonic anhydrase inhibitory properties of some uracil derivatives. Journal of Enzyme Inhibition and Medicinal Chemistry 32:1, pages 74-77.
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Chandra Bhushan Mishra, Shikha Kumari, Andrea Angeli, Simona Maria Monti, Martina Buonanno, Amresh Prakash, Manisha Tiwari & Claudiu T. Supuran. (2016) Design, synthesis and biological evaluation of N-(5-methyl-isoxazol-3-yl/1,3,4-thiadiazol-2-yl)-4-(3-substitutedphenylureido) benzenesulfonamides as human carbonic anhydrase isoenzymes I, II, VII and XII inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 31:sup2, pages 174-179.
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F. Zehra Küçükbay, Hasan Küçükbay, Muhammet Tanc & Claudiu T. Supuran. (2016) Synthesis and carbonic anhydrase I, II, IV and XII inhibitory properties of N-protected amino acid – sulfonamide conjugates. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1476-1483.
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Afsun Sujayev, Leyla Polat Kose, Emin Garibov, İlhami Gülçin, Vagif Farzaliev, Saleh H. Alwasel & Claudiu T. Supuran. (2016) Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects. Journal of Enzyme Inhibition and Medicinal Chemistry 31:6, pages 1192-1197.
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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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Articles from other publishers (22)

Claudiu T. Supuran. (2023) A simple yet multifaceted 90 years old, evergreen enzyme: Carbonic anhydrase, its inhibition and activation. Bioorganic & Medicinal Chemistry Letters 93, pages 129411.
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Hui Sun, Huijian Shang & Bin Cui. (2022) (Salen)Mn(III)-Catalyzed Enantioselective Intramolecular Haloamination of Alkenes through Chiral Aziridinium Ion Ring-Opening Sequence. ACS Catalysis 12:12, pages 7046-7053.
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Baijayantimala Swain, Santosh Kumar Sahoo, Priti Singh, Andrea Angeli, Venkata Madhavi Yaddanapudi, Claudiu T. Supuran & Mohammed Arifuddin. (2022) Exploration of 2-phenylquinoline-4-carboxamide linked benzene sulfonamide derivatives as isoform selective inhibitors of transmembrane human carbonic anhydrases. European Journal of Medicinal Chemistry 234, pages 114247.
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Fatma AYDIN, Zeynep Aleyna KAHRAMAN, Emir Alper TÜRKOĞLU, Müslüm KUZU & Zeki SEVEROĞLU. (2021) In vitro antioxidant activity and carbonic anhydrase inhibitory features of Ferula communis extracts. International Journal of Agriculture Environment and Food Sciences 5:4, pages 592-598.
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Baijayantimala Swain, Chander Singh Digwal, Andrea Angeli, Mallika Alvala, Priti Singh, Claudiu T. Supuran & Mohammed Arifuddin. (2019) Synthesis and exploration of 2-morpholino-4-phenylthiazol-5-yl acrylamide derivatives for their effects against carbonic anhydrase I, II, IX and XII isoforms as a non-sulfonamide class of inhibitors. Bioorganic & Medicinal Chemistry 27:21, pages 115090.
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Andrey V. Smolobochkin, Tanzilya S. Rizbayeva, Anna S. Melyashova, Alexander R. Burilov, Michail A. Pudovik, Oleg G. Sinyashin & Almir S. Gazizov. (2019) Acid‐Catalyzed Cascade Reaction of 4‐Aminobutanal Derivatives with (Hetero)aromatic Nucleophiles: A Versatile One‐Pot Access to 2‐(Hetero)arylpyrrolidines.. ChemistrySelect 4:32, pages 9322-9330.
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Simone Carradori & Paolo Guglielmi. 2019. Carbonic Anhydrases. Carbonic Anhydrases 257 268 .
Claudiu T. Supuran, Vincenzo Alterio, Anna Di Fiore, Katia D’ Ambrosio, Fabrizio Carta, Simona Maria Monti & Giuseppina De Simone. (2018) Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one. Medicinal Research Reviews 38:6, pages 1799-1836.
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Srinivas Angapelly, P.V. Sri Ramya, Andrea Angeli, Sonia Del Prete, Clemente Capasso, Mohammed Arifuddin & Claudiu T. Supuran. (2017) Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors. Bioorganic & Medicinal Chemistry 25:20, pages 5726-5732.
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Andrea Angeli, Alaa A.-M. Abdel-Aziz, Alessio Nocentini, Adel S. El-Azab, Paola Gratteri & Claudiu T. Supuran. (2017) Synthesis and carbonic anhydrase inhibition of polycyclic imides incorporating N-benzenesulfonamide moieties. Bioorganic & Medicinal Chemistry 25:20, pages 5373-5379.
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Claudiu T. Supuran. (2017) Bortezomib inhibits mammalian carbonic anhydrases. Bioorganic & Medicinal Chemistry 25:19, pages 5064-5067.
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Jekaterīna Ivanova, Fabrizio Carta, Daniela Vullo, Janis Leitans, Andris Kazaks, Kaspars Tars, Raivis Žalubovskis & Claudiu T. Supuran. (2017) N -Substituted and ring opened saccharin derivatives selectively inhibit transmembrane, tumor-associated carbonic anhydrases IX and XII. Bioorganic & Medicinal Chemistry 25:13, pages 3583-3589.
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Hélène Carreyre, Grégoire Carré, Maurice Ouedraogo, Clarisse Vandebrouck, Jocelyn Bescond, Claudiu T. Supuran & Sébastien Thibaudeau. (2017) Bioactive Natural Product and Superacid Chemistry for Lead Compound Identification: A Case Study of Selective hCA III and L-Type Ca2+ Current Inhibitors for Hypotensive Agent Discovery. Molecules 22:6, pages 915.
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Alaa A.-M. Abdel-Aziz, Andrea Angeli, Adel S. El-Azab, Mohamed A. Abu El-Enin & Claudiu T. Supuran. (2017) Synthesis and biological evaluation of cyclic imides incorporating benzenesulfonamide moieties as carbonic anhydrase I, II, IV and IX inhibitors. Bioorganic & Medicinal Chemistry 25:5, pages 1666-1671.
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Jekaterīna Ivanova, Agnese Balode, Raivis Žalubovskis, Janis Leitans, Andris Kazaks, Daniela Vullo, Kaspars Tars & Claudiu T. Supuran. (2017) 5-Substituted-benzylsulfanyl-thiophene-2-sulfonamides with effective carbonic anhydrase inhibitory activity: Solution and crystallographic investigations. Bioorganic & Medicinal Chemistry 25:3, pages 857-863.
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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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S. Thibaudeau, H. Carreyre & A. Mingot. 2017. Modern Synthesis Processes and Reactivity of Fluorinated Compounds. Modern Synthesis Processes and Reactivity of Fluorinated Compounds 349 388 .
Tayfun Arslan, Emir Alper Türkoğlu, Murat Şentürk & Claudiu T. Supuran. (2016) Synthesis and carbonic anhydrase inhibitory properties of novel chalcone substituted benzenesulfonamides. Bioorganic & Medicinal Chemistry Letters 26:24, pages 5867-5870.
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Sonia Del Prete, Daniela Vullo, Viviana De Luca, Vincenzo Carginale, Sameh M. Osman, Zeid AlOthman, Claudiu T. Supuran & Clemente Capasso. (2016) Cloning, expression, purification and sulfonamide inhibition profile of the complete domain of the η-carbonic anhydrase from Plasmodium falciparum. Bioorganic & Medicinal Chemistry Letters 26:17, pages 4184-4190.
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Claudiu T. Supuran. (2016) Bortezomib inhibits bacterial and fungal β-carbonic anhydrases. Bioorganic & Medicinal Chemistry 24:18, pages 4406-4409.
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Murat Bozdag, Ahmed M. Alafeefy, Fabrizio Carta, Mariangela Ceruso, Abdul-Malek S. Al-Tamimi, Abdulla A. Al-Kahtani, Fatmah A.S. Alasmary & Claudiu T. Supuran. (2016) Synthesis 4-[2-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-ethyl]-benzenesulfonamides with subnanomolar carbonic anhydrase II and XII inhibitory properties. Bioorganic & Medicinal Chemistry 24:18, pages 4100-4107.
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Alexandre Le Darz, Ugo Castelli, Naima Mokhtari, Agnès Martin-Mingot, Jérôme Marrot, Fodil Bouazza, Omar Karam & Sébastien Thibaudeau. (2016) Tandem superelectrophilic activation for the regioselective chlorofluorination of recalcitrant allylic amines. Tetrahedron 72:5, pages 674-689.
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