Literature DB >> 25147616

Carbonic Anhydrase Inhibition with Benzenesulfonamides and Tetrafluorobenzenesulfonamides Obtained via Click Chemistry.

Nicolino Pala1, Laura Micheletto1, Mario Sechi1, Mayank Aggarwal2, Fabrizio Carta3, Robert McKenna2, Claudiu T Supuran4.   

Abstract

A series of novel benzene- and 2,3,5,6-tetrafluorobenzenesulfonamide was synthesized by using a click chemistry approach starting from azido-substituted sulfonamides and alkynes, incorporating aryl, alkyl, cycloalkyl, and amino-/hydroxy-/halogenoalkyl moieties. The new compounds were medium potency inhibitors of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and low nanomolar/subnanomolar inhibitors of the tumor-associated hCA IX and XII isoforms. The X-ray crystal structure of two such sulfonamides in adduct with hCA II allowed us to understand the factors governing inhibitory power.

Entities:  

Keywords:  Carbonic anhydrase; benzenesulfonamide; click chemistry; human isoform I; human isoform II; human isoform IX; human isoform XII

Year:  2014        PMID： 25147616      PMCID： PMC4137363          DOI： 10.1021/ml500196t

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  17 in total

1.  Sulfonamides incorporating 1,3,5-triazine moieties selectively and potently inhibit carbonic anhydrase transmembrane isoforms IX, XII and XIV over cytosolic isoforms I and II: Solution and X-ray crystallographic studies.

Authors:  Fabrizio Carta; Vladimir Garaj; Alfonso Maresca; Jason Wagner; Balendu Sankara Avvaru; Arthur H Robbins; Andrea Scozzafava; Robert McKenna; Claudiu T Supuran
Journal:  Bioorg Med Chem       Date:  2011-04-06       Impact factor: 3.641

2.  Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II.

Authors:  Anna Di Fiore; Alfonso Maresca; Vincenzo Alterio; Claudiu T Supuran; Giuseppina De Simone
Journal:  Chem Commun (Camb)       Date:  2011-09-26       Impact factor: 6.222

Review 3.  Carbonic anhydrases: novel therapeutic applications for inhibitors and activators.

Authors:  Claudiu T Supuran
Journal:  Nat Rev Drug Discov       Date:  2008-02       Impact factor: 84.694

4.  Thiol-ene click chemistry for the synthesis of highly effective glycosyl sulfonamide carbonic anhydrase inhibitors.

Authors:  Mohamed-Chiheb Saada; Joanna Ombouma; Jean-Louis Montero; Claudiu T Supuran; Jean-Yves Winum
Journal:  Chem Commun (Camb)       Date:  2013-05-20       Impact factor: 6.222

5.  Targeting hypoxic tumor cell viability with carbohydrate-based carbonic anhydrase IX and XII inhibitors.

Authors:  Jason C Morris; Johanna Chiche; Caroline Grellier; Marie Lopez; Laurent F Bornaghi; Alfonso Maresca; Claudiu T Supuran; Jacques Pouysségur; Sally-Ann Poulsen
Journal:  J Med Chem       Date:  2011-09-02       Impact factor: 7.446

6.  5-Substituted-(1,2,3-triazol-4-yl)thiophene-2-sulfonamides strongly inhibit human carbonic anhydrases I, II, IX and XII: solution and X-ray crystallographic studies.

Authors:  Janis Leitans; Agnese Sprudza; Muhammet Tanc; Igor Vozny; Raivis Zalubovskis; Kaspars Tars; Claudiu T Supuran
Journal:  Bioorg Med Chem       Date:  2013-06-27       Impact factor: 3.641

7.  Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors.

Authors:  Balendu Sankara Avvaru; Jason M Wagner; Alfonso Maresca; Andrea Scozzafava; Arthur H Robbins; Claudiu T Supuran; Robert McKenna
Journal:  Bioorg Med Chem Lett       Date:  2010-06-17       Impact factor: 2.823

8.  Carbonic anhydrase inhibitors: perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure-lowering agents with prolonged duration of action.

Authors:  A Scozzafava; L Menabuoni; F Mincione; F Briganti; G Mincione; C T Supuran
Journal:  J Med Chem       Date:  2000-11-16       Impact factor: 7.446

9.  A small-molecule drug conjugate for the treatment of carbonic anhydrase IX expressing tumors.

Authors:  Nikolaus Krall; Francesca Pretto; Willy Decurtins; Gonçalo J L Bernardes; Claudiu T Supuran; Dario Neri
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-12       Impact factor: 15.336

10.  Carbonic anhydrase inhibitors: inhibition of isozymes I, II, and IX with triazole-linked O-glycosides of benzene sulfonamides.

Authors:  Brendan L Wilkinson; Laurent F Bornaghi; Todd A Houston; Alessio Innocenti; Daniela Vullo; Claudiu T Supuran; Sally-Ann Poulsen
Journal:  J Med Chem       Date:  2007-03-08       Impact factor: 7.446
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  11 in total

Review 1.  Thiazole Ring-A Biologically Active Scaffold.

Authors:  Anthi Petrou; Maria Fesatidou; Athina Geronikaki
Journal:  Molecules       Date:  2021-05-25       Impact factor: 4.411

2.  Tuning the Dual Inhibition of Carbonic Anhydrase and Cyclooxygenase by Dihydrothiazole Benzensulfonamides.

Authors:  Rita Meleddu; Simona Distinto; Filippo Cottiglia; Rossella Angius; Marco Gaspari; Domenico Taverna; Claudia Melis; Andrea Angeli; Giulia Bianco; Serenella Deplano; Benedetta Fois; Sonia Del Prete; Clemente Capasso; Stefano Alcaro; Francesco Ortuso; Matilde Yanez; Claudiu T Supuran; Elias Maccioni
Journal:  ACS Med Chem Lett       Date:  2018-09-17       Impact factor: 4.345

3.  Inhibitory Effect of 2,3,5,6-Tetrafluoro-4-[4-(aryl)-1H-1,2,3-triazol-1-yl]benzenesulfonamide Derivatives on HIV Reverse Transcriptase Associated RNase H Activities.

Authors:  Nicolino Pala; Francesca Esposito; Dominga Rogolino; Mauro Carcelli; Vanna Sanna; Michele Palomba; Lieve Naesens; Angela Corona; Nicole Grandi; Enzo Tramontano; Mario Sechi
Journal:  Int J Mol Sci       Date:  2016-08-20       Impact factor: 5.923

4.  Isatin: a privileged scaffold for the design of carbonic anhydrase inhibitors.

Authors:  Claudia Melis; Rita Meleddu; Andrea Angeli; Simona Distinto; Giulia Bianco; Clemente Capasso; Filippo Cottiglia; Rossella Angius; Claudiu T Supuran; Elias Maccioni
Journal:  J Enzyme Inhib Med Chem       Date:  2016-10-24       Impact factor: 5.051

5.  Novel Re(I) tricarbonyl coordination compounds based on 2-pyridyl-1,2,3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I, II, and IX isoforms†.

Authors:  Yassine Aimene; Romain Eychenne; Sonia Mallet-Ladeira; Nathalie Saffon; Jean-Yves Winum; Alessio Nocentini; Claudiu T Supuran; Eric Benoist; Achour Seridi
Journal:  J Enzyme Inhib Med Chem       Date:  2019-12       Impact factor: 5.051

6.  Exploring new structural features of the 4-[(3-methyl-4-aryl-2,3-dihydro-1,3-thiazol-2-ylidene)amino]benzenesulphonamide scaffold for the inhibition of human carbonic anhydrases.

Authors:  Simona Distinto; Rita Meleddu; Francesco Ortuso; Filippo Cottiglia; Serenella Deplano; Lisa Sequeira; Claudia Melis; Benedetta Fois; Andrea Angeli; Clemente Capasso; Rossella Angius; Stefano Alcaro; Claudiu T Supuran; Elias Maccioni
Journal:  J Enzyme Inhib Med Chem       Date:  2019-12       Impact factor: 5.051

7.  Synthesis, Bioactivity Assessment, and Molecular Docking of Non-sulfonamide Benzimidazole-Derived N-Acylhydrazone Scaffolds as Carbonic Anhydrase-II Inhibitors.

Authors:  Muhammad Saadiq; Ghias Uddin; Abdul Latif; Mumtaz Ali; Nazia Akbar; Sardar Ali; Manzoor Ahmad; Mohammad Zahoor; Ajmal Khan; Ahmed Al-Harrasi
Journal:  ACS Omega       Date:  2021-12-20

8.  Diversely substituted sulfamides for fragment-based drug discovery of carbonic anhydrase inhibitors: synthesis and inhibitory profile.

Authors:  Tatiana Sharonova; Petr Zhmurov; Stanislav Kalinin; Alessio Nocentini; Andrea Angeli; Marta Ferraroni; Mikhail Korsakov; Claudiu T Supuran; Mikhail Krasavin
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.051

Review 9.  Microbial Carbonic Anhydrases in Biomimetic Carbon Sequestration for Mitigating Global Warming: Prospects and Perspectives.

Authors:  Himadri Bose; Tulasi Satyanarayana
Journal:  Front Microbiol       Date:  2017-08-25       Impact factor: 5.640

10.  Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors.

Authors:  P V Sri Ramya; Srinivas Angapelly; Andrea Angeli; Chander Singh Digwal; Mohammed Arifuddin; Bathini Nagendra Babu; Claudiu T Supuran; Ahmed Kamal
Journal:  J Enzyme Inhib Med Chem       Date:  2017-12       Impact factor: 5.051
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