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Current Topics in Medicinal Chemistry

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ISSN (Online): 1873-4294

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Review Article

Recent Advances in the Design and Synthesis of Small Molecule Carbonic Anhydrase IX Inhibitors

Author(s): Pengcheng Lv*, Yinyi Cai, Jiayi Luo and Kun Chen*

Volume 22, Issue 7, 2022

Published on: 12 April, 2022

Page: [550 - 560] Pages: 11

DOI: 10.2174/1568026622666220215104312

Price: $65

Abstract

Human carbonic anhydrase (CA) IX is a tumor-associated protein since it is scarcely present in normal tissues but highly overexpressed in a large number of solid tumors, where it actively contributes to survival and metastatic spread of tumor cells. A variety of approaches and design strategies were reported that afford CA IX/XII specific inhibitors and avoid the compromising effects of isoforms-promiscuous compounds. CA IX inhibitors hybrids/conjugates have become an important scaffold to design therapeutic agents with both CA inhibition and anti-cancer effects. In this review, we firstly present an overview of the role of CA IX in hypoxic tumors physiopathology, then provide a comprehensive update on the rational design and synthesis of small molecule CA IX inhibitors discovered since 2019. Also, their structure-activity relationship analysis studies are covered. A brief description of applications for CA IX inhibition in other therapeutic areas is also provided.

Keywords: Carbonic anhydrases, pH regulation, CA IX inhibitors, Tumour hypoxia, Hypoxia inducible factor 1 (HIF1), Tumor- associated protein.

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Graphical Abstract

[1]
Supuran, C.T. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discov., 2008, 7(2), 168-181.
[http://dx.doi.org/10.1038/nrd2467] [PMID: 18167490]
[2]
Alterio, V.; Di Fiore, A.; D’Ambrosio, K.; Supuran, C.T.; De Simone, G. Multiple binding modes of inhibitors to carbonic anhydrases: How to design specific drugs targeting 15 different isoforms? Chem. Rev., 2012, 112(8), 4421-4468.
[http://dx.doi.org/10.1021/cr200176r] [PMID: 22607219]
[3]
De Simone, G.; Alterio, V.; Supuran, C.T. Exploiting the hydrophobic and hydrophilic binding sites for designing carbonic anhydrase inhibitors. Expert Opin. Drug Discov., 2013, 8(7), 793-810.
[http://dx.doi.org/10.1517/17460441.2013.795145] [PMID: 23627619]
[4]
Supuran, C.T.; Alterio, V.; Di Fiore, A.; D’ Ambrosio, K.; Carta, F.; Monti, S.M.; De Simone, G. Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one. Med. Res. Rev., 2018, 38(6), 1799-1836.
[http://dx.doi.org/10.1002/med.21497] [PMID: 29635752]
[5]
Aggarwal, M.; Boone, C.D.; Kondeti, B.; McKenna, R. Structural annotation of human carbonic anhydrases. J. Enzyme Inhib. Med. Chem., 2013, 28(2), 267-277.
[http://dx.doi.org/10.3109/14756366.2012.737323] [PMID: 23137351]
[6]
Supuran, C.T. Structure and function of carbonic anhydrases. Biochem. J., 2016, 473(14), 2023-2032.
[http://dx.doi.org/10.1042/BCJ20160115] [PMID: 27407171]
[7]
Neri, D.; Supuran, C.T. Interfering with pH regulation in tumours as a therapeutic strategy. Nat. Rev. Drug Discov., 2011, 10(10), 767-777.
[http://dx.doi.org/10.1038/nrd3554] [PMID: 21921921]
[8]
Supuran, C.T. How many carbonic anhydrase inhibition mechanisms exist? J. Enzyme Inhib. Med. Chem., 2016, 31(3), 345-360.
[http://dx.doi.org/10.3109/14756366.2015.1122001] [PMID: 26619898]
[9]
Supuran, C.T. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opin. Investig. Drugs, 2018, 27(12), 963-970.
[http://dx.doi.org/10.1080/13543784.2018.1548608] [PMID: 30426805]
[10]
Supuran, C.T. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin. Drug Discov., 2017, 12(1), 61-88.
[http://dx.doi.org/10.1080/17460441.2017.1253677] [PMID: 27783541]
[11]
Berrino, E.; Supuran, C.T. Novel approaches for designing drugs that interfere with pH regulation. Expert Opin. Drug Discov., 2019, 14(3), 231-248.
[http://dx.doi.org/10.1080/17460441.2019.1567488] [PMID: 30681011]
[12]
Supuran, C.T. Carbonic anhydrase inhibitors and their potential in a range of therapeutic areas. Expert Opin. Ther. Pat., 2018, 28(10), 709-712.
[http://dx.doi.org/10.1080/13543776.2018.1523897] [PMID: 30217119]
[13]
Vullo, D.; Franchi, M.; Gallori, E.; Pastorek, J.; Scozzafava, A.; Pastorekova, S.; Supuran, C.T. Carbonic anhydrase inhibitors: Inhibition of the tumor-associated isozyme IX with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett., 2003, 13(6), 1005-1009.
[http://dx.doi.org/10.1016/S0960-894X(03)00091-X] [PMID: 12643899]
[14]
Vullo, D.; Innocenti, A.; Nishimori, I.; Pastorek, J.; Scozzafava, A.; Pastoreková, S.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett., 2005, 15(4), 963-969.
[http://dx.doi.org/10.1016/j.bmcl.2004.12.053] [PMID: 15686894]
[15]
Lehtonen, J.; Shen, B.; Vihinen, M.; Casini, A.; Scozzafava, A.; Supuran, C.T.; Parkkila, A.K.; Saarnio, J.; Kivelä, A.J.; Waheed, A.; Sly, W.S.; Parkkila, S. Characterization of CA XIII, a novel member of the carbonic anhydrase isozyme family. J. Biol. Chem., 2004, 279(4), 2719-2727.
[http://dx.doi.org/10.1074/jbc.M308984200] [PMID: 14600151]
[16]
Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Carbonic anhydrase inhibitors: Inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg. Med. Chem. Lett., 2005, 15(17), 3828-3833.
[http://dx.doi.org/10.1016/j.bmcl.2005.06.055] [PMID: 16039848]
[17]
Stams, T.; Christianson, D.W. The Carbonic Anhydrases - New Horizons; Chegwidden, W.R.; Carter, N.D.; Edwards, Y.H., Eds.; Birkhauser: Basel, 2000, pp. 159-174.
[http://dx.doi.org/10.1007/978-3-0348-8446-4_9]
[18]
Pastorekova, S.; Parkkila, S.; Pastorek, J.; Supuran, C.T. Carbonic anhydrases: Current state of the art, therapeutic applications and future prospects. J. Enzyme Inhib. Med. Chem., 2004, 19(3), 199-229.
[http://dx.doi.org/10.1080/14756360410001689540] [PMID: 15499993]
[19]
Nishimori, I.; Minakuchi, T.; Onishi, S.; Vullo, D.; Cecchi, A.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: Cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg. Med. Chem., 2007, 15(23), 7229-7236.
[http://dx.doi.org/10.1016/j.bmc.2007.08.037] [PMID: 17826101]
[20]
Vullo, D.; Franchi, M.; Gallori, E.; Antel, J.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J. Med. Chem., 2004, 47(5), 1272-1279.
[http://dx.doi.org/10.1021/jm031057+] [PMID: 14971907]
[21]
Alterio, V.; Vitale, R.M.; Monti, S.M.; Pedone, C.; Scozzafava, A.; Cecchi, A.; De Simone, G.; Supuran, C.T. Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX. J. Am. Chem. Soc., 2006, 128(25), 8329-8335.
[http://dx.doi.org/10.1021/ja061574s] [PMID: 16787097]
[22]
De Simone, G.; Di Fiore, A.; Supuran, C.T. Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs? Curr. Pharm. Des., 2008, 14(7), 655-660.
[http://dx.doi.org/10.2174/138161208783877820] [PMID: 18336311]
[23]
De Simone, G.; Supuran, C.T. Antiobesity carbonic anhydrase inhibitors. Curr. Top. Med. Chem., 2007, 7(9), 879-884.
[http://dx.doi.org/10.2174/156802607780636762] [PMID: 17504132]
[24]
Supuran, C.T.; Di Fiore, A.; De Simone, G. Carbonic anhydrase inhibitors as emerging drugs for the treatment of obesity. Expert Opin. Emerg. Drugs, 2008, 13(2), 383-392.
[http://dx.doi.org/10.1517/14728214.13.2.383] [PMID: 18537527]
[25]
Winum, J-Y.; Rami, M.; Scozzafava, A.; Montero, J-L.; Supuran, C. Carbonic anhydrase IX: A new druggable target for the design of antitumor agents. Med. Res. Rev., 2008, 28(3), 445-463.
[http://dx.doi.org/10.1002/med.20112] [PMID: 17880011]
[26]
Guler, O.O.; De Simone, G.; Supuran, C.T. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr. Med. Chem., 2010, 17(15), 1516-1526.
[http://dx.doi.org/10.2174/092986710790979999] [PMID: 20166929]
[27]
Köhler, K.; Hillebrecht, A.; Schulze Wischeler, J.; Innocenti, A.; Heine, A.; Supuran, C.T.; Klebe, G. Saccharin inhibits carbonic anhydrases: Possible explanation for its unpleasant metallic aftertaste. Angew. Chem. Int. Ed., 2007, 46(40), 7697-7699.
[http://dx.doi.org/10.1002/anie.200701189] [PMID: 17705204]
[28]
Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin. Ther. Pat., 2006, 16(12), 1627-1664.
[http://dx.doi.org/10.1517/13543776.16.12.1627]
[29]
Supuran, C.T.; Scozzafava, A.; Casini, A. Carbonic anhydrase inhibitors. Med. Res. Rev., 2003, 23(2), 146-189.
[http://dx.doi.org/10.1002/med.10025] [PMID: 12500287]
[30]
Smith, K.S.; Ferry, J.G. Prokaryotic carbonic anhydrases. FEMS Microbiol. Rev., 2000, 24(4), 335-366.
[http://dx.doi.org/10.1111/j.1574-6976.2000.tb00546.x] [PMID: 10978542]
[31]
Thiry, A.; Dogné, J.M.; Masereel, B.; Supuran, C.T. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol. Sci., 2006, 27(11), 566-573.
[http://dx.doi.org/10.1016/j.tips.2006.09.002] [PMID: 16996620]
[32]
Supuran, C.T.; Ilies, M.A.; Scozzafava, A. Carbonic anhydrase inhibitors. Part 29. Interaction of isozymes I, II and IV with benzolamide-like derivatives. Eur. J. Med. Chem., 1998, 33(9), 739-752.
[http://dx.doi.org/10.1016/S0223-5234(98)80042-1]
[33]
Supuran, C.T.; Scozzafava, A.; Ilies, M.A.; Briganti, F. Carbonic anhydrase inhibitors: Synthesis of sulfonamides incorporating 2,4,6-trisubstituted-pyridinium-ethylcarboxamido moieties possessing membrane-impermeability and in vivo selectivity for the membrane-bound (CA IV) versus the cytosolic (CA I and CA II) isozymes. J. Enzyme Inhib., 2000, 15(4), 381-401.
[http://dx.doi.org/10.1080/14756360009040695] [PMID: 10995069]
[34]
Scozzafava, A.; Briganti, F.; Ilies, M.A.; Supuran, C.T. Carbonic anhydrase inhibitors: Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J. Med. Chem., 2000, 43(2), 292-300.
[http://dx.doi.org/10.1021/jm990479+] [PMID: 10649985]
[35]
Winum, J.Y.; Temperini, C.; El Cheikh, K.; Innocenti, A.; Vullo, D.; Ciattini, S.; Montero, J.L.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors: Clash with Ala65 as a means for designing inhibitors with low affinity for the ubiquitous isozyme II, exemplified by the crystal structure of the topiramate sulfamide analogue. J. Med. Chem., 2006, 49(24), 7024-7031.
[http://dx.doi.org/10.1021/jm060807n] [PMID: 17125255]
[36]
Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. J. Med. Chem., 2005, 48(24), 7860-7866.
[http://dx.doi.org/10.1021/jm050483n] [PMID: 16302824]
[37]
Supuran, C.T.; Scozzafava, A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg. Med. Chem., 2007, 15(13), 4336-4350.
[http://dx.doi.org/10.1016/j.bmc.2007.04.020] [PMID: 17475500]
[38]
Nishimori, I.; Minakuchi, T.; Onishi, S.; Vullo, D.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J. Med. Chem., 2007, 50(2), 381-388.
[http://dx.doi.org/10.1021/jm0612057] [PMID: 17228881]
[39]
Vullo, D.; Voipio, J.; Innocenti, A.; Rivera, C.; Ranki, H.; Scozzafava, A.; Kaila, K.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett., 2005, 15(4), 971-976.
[http://dx.doi.org/10.1016/j.bmcl.2004.12.052] [PMID: 15686895]
[40]
Nishimori, I. Carbonic anhydrase - its inhibitors and activators; Supuran, C.T.; Scozzafava, A.; Conway, J., Eds.; CRC: Boca Raton, 2004, pp. 25-43.
[http://dx.doi.org/10.1201/9780203475300.ch2]
[41]
Saczewski, F.; Sławiński, J.; Kornicka, A.; Brzozowski, Z.; Pomarnacka, E.; Innocenti, A.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of the cytosolic human isozymes I and II, and the transmembrane, tumor-associated isozymes IX and XII with substituted aromatic sulfonamides activatable in hypoxic tumors. Bioorg. Med. Chem. Lett., 2006, 16(18), 4846-4851.
[http://dx.doi.org/10.1016/j.bmcl.2006.06.064] [PMID: 16809036]
[42]
De Simone, G.; Vitale, R.M.; Di Fiore, A.; Pedone, C.; Scozzafava, A.; Montero, J.L.; Winum, J.Y.; Supuran, C.T. Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX. J. Med. Chem., 2006, 49(18), 5544-5551.
[http://dx.doi.org/10.1021/jm060531j] [PMID: 16942027]
[43]
Supuran, C.T. Carbonic anhydrases as drug targets--an overview. Curr. Top. Med. Chem., 2007, 7(9), 825-833.
[http://dx.doi.org/10.2174/156802607780636690] [PMID: 17504127]
[44]
Scozzafava, A.; Mastrolorenzo, A.; Supuran, C.T. Modulation of carbonic anhydrase activity and its applications in therapy. Expert Opin. Ther. Pat., 2004, 14(5), 667-702.
[http://dx.doi.org/10.1517/13543776.14.5.667]
[45]
Winum, J-Y.; Scozzafava, A.; Montero, J-L.; Supuran, C.T. New zinc binding motifs in the design of selective carbonic anhydrase inhibitors. Mini Rev. Med. Chem., 2006, 6(8), 921-936.
[http://dx.doi.org/10.2174/138955706777934946] [PMID: 16918498]
[46]
Temperini, C.; Scozzafava, A.; Supuran, C.T. Drug design of zincenzyme inhibitors: functional, structural, and disease applications;; Supuran, C.T.; Winum, J-Y., Eds.; Wiley: Hoboken, NJ, 2009, p. 473.
[http://dx.doi.org/10.1002/9780470508169.ch22]
[47]
Thiry, A.; Dogné, J.M.; Supuran, C.T.; Masereel, B. Anticonvulsant sulfonamides/sulfamates/sulfamides with carbonic anhydrase inhibitory activity: Drug design and mechanism of action. Curr. Pharm. Des., 2008, 14(7), 661-671.
[http://dx.doi.org/10.2174/138161208783877956] [PMID: 18336312]
[48]
Hen, N.; Bialer, M.; Yagen, B.; Maresca, A.; Aggarwal, M.; Robbins, A.H.; McKenna, R.; Scozzafava, A.; Supuran, C.T. Anticonvulsant 4-aminobenzenesulfonamide derivatives with branched-alkylamide moieties: X-ray crystallography and inhibition studies of human carbonic anhydrase isoforms I, II, VII, and XIV. J. Med. Chem., 2011, 54(11), 3977-3981.
[http://dx.doi.org/10.1021/jm200209n] [PMID: 21506569]
[49]
K€ohler, K.; Hillebrecht, A.S.; Wischeler, J. Saccharin inhibits carbonic anhydrases: Possible explanation for its unpleasant metallic aftertaste. Angew. Chem. Int. Ed. Engl., 2007, 46, 7697-7699.
[50]
Jensen, E.L.; Clement, R.; Kosta, A.; Maberly, S.C.; Gontero, B. A new widespread subclass of carbonic anhydrase in marine phytoplankton. ISME J., 2019, 13(8), 2094-2106.
[http://dx.doi.org/10.1038/s41396-019-0426-8] [PMID: 31024153]
[51]
Carta, F.; Supuran, C.T. Diuretics with carbonic anhydrase inhibitory action: A patent and literature review (2005 - 2013). Expert Opin. Ther. Pat., 2013, 23(6), 681-691.
[http://dx.doi.org/10.1517/13543776.2013.780598] [PMID: 23488823]
[52]
Carta, F.; Supuran, C.T.; Scozzafava, A. Novel therapies for glaucoma: A patent review 2007 - 2011. Expert Opin. Ther. Pat., 2012, 22(1), 79-88.
[http://dx.doi.org/10.1517/13543776.2012.649006] [PMID: 22191414]
[53]
Masini, E.; Carta, F.; Scozzafava, A.; Supuran, C.T. Antiglaucoma carbonic anhydrase inhibitors: A patent review. Expert Opin. Ther. Pat., 2013, 23(6), 705-716.
[http://dx.doi.org/10.1517/13543776.2013.794788] [PMID: 23627893]
[54]
Aggarwal, M.; Kondeti, B.; McKenna, R. Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: A patent review. Expert Opin. Ther. Pat., 2013, 23(6), 717-724.
[http://dx.doi.org/10.1517/13543776.2013.782394] [PMID: 23514045]
[55]
Scozzafava, A.; Supuran, C.T.; Carta, F. Antiobesity carbonic anhydrase inhibitors: A literature and patent review. Expert Opin. Ther. Pat., 2013, 23(6), 725-735.
[http://dx.doi.org/10.1517/13543776.2013.790957] [PMID: 23607332]
[56]
Supuran, C.T. Applications of carbonic anhydrases inhibitors in renal and central nervous system diseases. Expert Opin. Ther. Pat., 2018, 28(10), 713-721.
[http://dx.doi.org/10.1080/13543776.2018.1519023] [PMID: 30175635]
[57]
Supuran, C.T. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev. Neurother., 2015, 15(8), 851-856.
[http://dx.doi.org/10.1586/14737175.2015.1066675] [PMID: 26154918]
[58]
Carta, F.; Di Cesare Mannelli, L.; Pinard, M.; Ghelardini, C.; Scozzafava, A.; McKenna, R.; Supuran, C.T. A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects. Bioorg. Med. Chem., 2015, 23(8), 1828-1840.
[http://dx.doi.org/10.1016/j.bmc.2015.02.027] [PMID: 25766630]
[59]
Supuran, C.T. Carbonic anhydrase inhibition and the management of neuropathic pain. Expert Rev. Neurother., 2016, 16(8), 961-968.
[http://dx.doi.org/10.1080/14737175.2016.1193009] [PMID: 27211329]
[60]
Di Cesare Mannelli, L.; Micheli, L.; Carta, F.; Cozzi, A.; Ghelardini, C.; Supuran, C.T. Carbonic anhydrase inhibition for the management of cerebral ischemia: In vivo evaluation of sulfonamide and coumarin inhibitors. J. Enzyme Inhib. Med. Chem., 2016, 31(6), 894-899.
[http://dx.doi.org/10.3109/14756366.2015.1113407] [PMID: 26607399]
[61]
Margheri, F.; Ceruso, M.; Carta, F.; Laurenzana, A.; Maggi, L.; Lazzeri, S.; Simonini, G.; Annunziato, F.; Del Rosso, M.; Supuran, C.T.; Cimaz, R. Overexpression of the transmembrane carbonic anhydrase isoforms IX and XII in the inflamed synovium. J. Enzyme Inhib. Med. Chem., 2016, 31(sup4), 60-63.
[http://dx.doi.org/10.1080/14756366.2016.1217857] [PMID: 27539792]
[62]
Bua, S.; Di Cesare Mannelli, L.; Vullo, D.; Ghelardini, C.; Bartolucci, G.; Scozzafava, A.; Supuran, C.T.; Carta, F. Design and synthesis of novel nonsteroidal anti-inflammatory drugs and carbonic anhydrase inhibitors hybrids (NSAIDs-CAIs) for the treatment of rheumatoid arthritis. J. Med. Chem., 2017, 60(3), 1159-1170.
[http://dx.doi.org/10.1021/acs.jmedchem.6b01607] [PMID: 28075587]
[63]
Akgul, O.; Di Cesare Mannelli, L.; Vullo, D.; Angeli, A.; Ghelardini, C.; Bartolucci, G.; Alfawaz Altamimi, A.S.; Scozzafava, A.; Supuran, C.T.; Carta, F. Discovery of novel nonsteroidal anti-inflammatory drugs and carbonic anhydrase inhibitors hybrids (NSAIDs-CAIs) for the management of rheumatoid arthritis. J. Med. Chem., 2018, 61(11), 4961-4977.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00420] [PMID: 29746127]
[64]
Mahon, B.P.; Hendon, A.M.; Driscoll, J.M.; Rankin, G.M.; Poulsen, S.A.; Supuran, C.T.; McKenna, R. Saccharin: A lead compound for structure-based drug design of carbonic anhydrase IX inhibitors. Bioorg. Med. Chem., 2015, 23(4), 849-854.
[http://dx.doi.org/10.1016/j.bmc.2014.12.030] [PMID: 25614109]
[65]
Koruza, K.; Mahon, B.P.; Blakeley, M.P.; Ostermann, A.; Schrader, T.E.; McKenna, R.; Knecht, W.; Fisher, S.Z. Using neutron crystallography to elucidate the basis of selective inhibition of carbonic anhydrase by saccharin and a derivative. J. Struct. Biol., 2019, 205(2), 147-154.
[http://dx.doi.org/10.1016/j.jsb.2018.12.009] [PMID: 30639924]
[66]
Murray, A.B.; Lomelino, C.L.; Supuran, C.T.; McKenna, R. “Seriously sweet”: Acesulfame K exhibits selective inhibition using alternative binding modes in carbonic anhydrase isoforms. J. Med. Chem., 2018, 61(3), 1176-1181.
[http://dx.doi.org/10.1021/acs.jmedchem.7b01470] [PMID: 29266943]
[67]
Carradori, S.; Secci, D.; De Monte, C.; Mollica, A.; Ceruso, M.; Akdemir, A.; Sobolev, A.P.; Codispoti, R.; De Cosmi, F.; Guglielmi, P.; Supuran, C.T. A novel library of saccharin and acesulfame derivatives as potent and selective inhibitors of carbonic anhydrase IX and XII isoforms. Bioorg. Med. Chem., 2016, 24(5), 1095-1105.
[http://dx.doi.org/10.1016/j.bmc.2016.01.038] [PMID: 26810710]
[68]
De Monte, C.; Carradori, S.; Secci, D.; D’Ascenzio, M.; Vullo, D.; Ceruso, M.; Supuran, C.T. Cyclic tertiary sulfamates: Selective inhibition of the tumor-associated carbonic anhydrases IX and XII by N- and O-substituted acesulfame derivatives. Eur. J. Med. Chem., 2014, 84, 240-246.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.014] [PMID: 25019479]
[69]
Nocentini, A.; Vullo, D.; Bartolucci, G.; Supuran, C.T. N-Nitrosulfonamides: A new chemotype for carbonic anhydrase inhibition. Bioorg. Med. Chem., 2016, 24(16), 3612-3617.
[http://dx.doi.org/10.1016/j.bmc.2016.05.072] [PMID: 27290692]
[70]
Tugrak, M.; Gul, H.I.; Bandow, K.; Sakagami, H.; Gulcin, I.; Ozkay, Y.; Supuran, C.T. Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors. Bioorg. Chem., 2019, 90, 103095.
[http://dx.doi.org/10.1016/j.bioorg.2019.103095] [PMID: 31288135]
[71]
Bilginer, S.; Gonder, B.; Gul, H.I.; Kaya, R.; Gulcin, I.; Anil, B.; Supuran, C.T. Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 325-329.
[http://dx.doi.org/10.1080/14756366.2019.1700240] [PMID: 31813300]
[72]
Sentürk, M.; Gülçin, I.; Daştan, A.; Küfrevioğlu, O.I.; Supuran, C.T. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg. Med. Chem., 2009, 17(8), 3207-3211.
[http://dx.doi.org/10.1016/j.bmc.2009.01.067] [PMID: 19231207]
[73]
Sarikaya, S.B.; Gülçin, I.; Supuran, C.T. Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem. Biol. Drug Des., 2010, 75(5), 515-520.
[http://dx.doi.org/10.1111/j.1747-0285.2010.00965.x] [PMID: 20486938]
[74]
Angeli, A.; Ferraroni, M.; Supuran, C.T. Famotidine, an Antiulcer Agent, Strongly Inhibits Helicobacter pylori and Human Carbonic Anhydrases. ACS Med. Chem. Lett., 2018, 9(10), 1035-1038.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00334] [PMID: 30344913]
[75]
Khloya, P.; Celik, G. SitaRam; Vullo, D.; Supuran, C.T.; Sharma, P.K. 4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII. Eur. J. Med. Chem., 2014, 76, 284-290.
[http://dx.doi.org/10.1016/j.ejmech.2014.02.023] [PMID: 24589484]
[76]
Kurt, B.Z.; Dag, A.; Doğan, B.; Durdagi, S.; Angeli, A.; Nocentini, A.; Supuran, C.T.; Sonmez, F. Synthesis, biological activity and multiscale molecular modeling studies of bis-coumarins as selective carbonic anhydrase IX and XII inhibitors with effective cytotoxicity against hepatocellular carcinoma. Bioorg. Chem., 2019, 87, 838-850.
[http://dx.doi.org/10.1016/j.bioorg.2019.03.003] [PMID: 31003041]
[77]
Chiaramonte, N.; Bua, S.; Angeli, A.; Ferraroni, M.; Picchioni, I.; Bartolucci, G.; Braconi, L.; Dei, S.; Teodori, E.; Supuran, C.T.; Romanelli, M.N. Sulfonamides incorporating piperazine bioisosteres as potent human carbonic anhydrase I, II, IV and IX inhibitors. Bioorg. Chem., 2019, 91, 103130.
[http://dx.doi.org/10.1016/j.bioorg.2019.103130] [PMID: 31374520]
[78]
Akocak, S.; Supuran, C.T. Activation of α-, β-, γ- δ-, ζ- and η- class of carbonic anhydrases with amines and amino acids: A review. J. Enzyme Inhib. Med. Chem., 2019, 34(1), 1652-1659.
[http://dx.doi.org/10.1080/14756366.2019.1664501] [PMID: 31530034]
[79]
Arabaci, B.; Gulcin, I.; Alwasel, S. Capsaicin: A potent inhibitor of carbonic anhydrase isoenzymes. Molecules, 2014, 19(7), 10103-10114.
[http://dx.doi.org/10.3390/molecules190710103] [PMID: 25014536]
[80]
Nocentini, A.; Bua, S.; Lomelino, C.L.; McKenna, R.; Menicatti, M.; Bartolucci, G.; Tenci, B.; Di Cesare Mannelli, L.; Ghelardini, C.; Gratteri, P.; Supuran, C.T. Discovery of new sulfonamide carbonic anhydrase IX inhibitors incorporating nitrogenous bases. ACS Med. Chem. Lett., 2017, 8(12), 1314-1319.
[http://dx.doi.org/10.1021/acsmedchemlett.7b00399] [PMID: 29259754]
[81]
Pałasz, A.; Cież, D. In search of uracil derivatives as bioactive agents. Uracils and fused uracils: Synthesis, biological activity and applications. Eur. J. Med. Chem., 2015, 97, 582-611.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.008] [PMID: 25306174]
[82]
Legraverend, M.; Grierson, D.S. The purines: Potent and versatile small molecule inhibitors and modulators of key biological targets. Bioorg. Med. Chem., 2006, 14(12), 3987-4006.
[http://dx.doi.org/10.1016/j.bmc.2005.12.060] [PMID: 16503144]
[83]
Parker, W.B. Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer. Chem. Rev., 2009, 109(7), 2880-2893.
[http://dx.doi.org/10.1021/cr900028p] [PMID: 19476376]
[84]
Calderón-Arancibia, J.; Espinosa-Bustos, C.; Cañete-Molina, Á.; Tapia, R.A.; Faúndez, M.; Torres, M.J.; Aguirre, A.; Paulino, M.; Salas, C.O. Synthesis and pharmacophore modelling of 2,6,9-trisubstituted purine derivatives and their potential role as apoptosis-inducing agents in cancer cell lines. Molecules, 2015, 20(4), 6808-6826.
[http://dx.doi.org/10.3390/molecules20046808] [PMID: 25884555]
[85]
Longley, D.B.; Harkin, D.P.; Johnston, P.G. 5-fluorouracil: Mechanisms of action and clinical strategies. Nat. Rev. Cancer, 2003, 3(5), 330-338.
[http://dx.doi.org/10.1038/nrc1074] [PMID: 12724731]
[86]
Gediya, L.K.; Njar, V.C. Promise and challenges in drug discovery and development of hybrid anticancer drugs. Expert Opin. Drug Discov., 2009, 4(11), 1099-1111.
[http://dx.doi.org/10.1517/17460440903341705] [PMID: 23480431]
[87]
Khalifah, R.G. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J. Biol. Chem., 1971, 246(8), 2561-2573.
[http://dx.doi.org/10.1016/S0021-9258(18)62326-9] [PMID: 4994926]
[88]
Nocentini, A.; Ceruso, M.; Bua, S.; Lomelino, C.L.; Andring, J.T.; McKenna, R.; Lanzi, C.; Sgambellone, S.; Pecori, R.; Matucci, R.; Filippi, L.; Gratteri, P.; Carta, F.; Masini, E.; Selleri, S.; Supuran, C.T. Discovery of β-adrenergic receptors blocker-carbonic anhydrase inhibitor hybrids for multitargeted antiglaucoma therapy. J. Med. Chem., 2018, 61(12), 5380-5394.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00625] [PMID: 29851481]
[89]
Nocentini, A.; Gratteri, P.; Supuran, C.T. Phosphorus versus sulfur: Discovery of benzenephosphonamidates as versatile sulfonamide-mimic chemotypes acting as carbonic anhydrase inhibitors. Chemistry, 2019, 25(5), 1188-1192.
[PMID: 30411821]
[90]
Nocentini, A.; Trallori, E.; Singh, S.; Lomelino, C.L.; Bartolucci, G.; Di Cesare Mannelli, L.; Ghelardini, C.; McKenna, R.; Gratteri, P.; Supuran, C.T. 4-Hydroxy-3-nitro-5-ureidobenzenesulfonamides selectively target the tumor-associated carbonic anhydrase isoforms IX and XII showing hypoxia-enhanced antiproliferative profiles. J. Med. Chem., 2018, 61(23), 10860-10874.
[http://dx.doi.org/10.1021/acs.jmedchem.8b01504] [PMID: 30433782]
[91]
Pinard, M.A.; Boone, C.D.; Rife, B.D.; Supuran, C.T.; McKenna, R. Structural study of interaction between brinzolamide and dorzolamide inhibition of human carbonic anhydrases. Bioorg. Med. Chem., 2013, 21(22), 7210-7215.
[http://dx.doi.org/10.1016/j.bmc.2013.08.033] [PMID: 24090602]
[92]
Eldehna, W.M.; Abo-Ashour, M.F.; Nocentini, A.; El-Haggar, R.S.; Bua, S.; Bonardi, A.; Al-Rashood, S.T.; Hassan, G.S.; Gratteri, P.; Abdel-Aziz, H.A.; Supuran, C.T. Enhancement of the tail hydrophobic interactions within the carbonic anhydrase IX active site via structural extension: Design and synthesis of novel N-substituted isatins-SLC-0111 hybrids as carbonic anhydrase inhibitors and antitumor agents. Eur. J. Med. Chem., 2019, 162, 147-160.
[http://dx.doi.org/10.1016/j.ejmech.2018.10.068] [PMID: 30445264]
[93]
Eldehna, W.M.; Abdelrahman, M.A.; Nocentini, A.; Bua, S.; Al-Rashood, S.T.; Hassan, G.S.; Bonardi, A.; Almehizia, A.A.; Alkahtani, H.M.; Alharbi, A.; Gratteri, P.; Supuran, C.T. Synthesis, biological evaluation and in silico studies with 4-benzylidene-2-phenyl-5(4H)-imidazolone-based benzenesulfonamides as novel selective carbonic anhydrase IX inhibitors endowed with anticancer activity. Bioorg. Chem., 2019, 90, 103102.
[http://dx.doi.org/10.1016/j.bioorg.2019.103102] [PMID: 31299596]
[94]
Abdelrahman, M.A.; Eldehna, W.M.; Nocentini, A.; Bua, S.; Al-Rashood, S.T.; Hassan, G.S.; Bonardi, A.; Almehizia, A.A.; Alkahtani, H.M.; Alharbi, A.; Gratteri, P.; Supuran, C.T. Novel diamide-based benzenesulfonamides as selective carbonic anhydrase IX inhibitors endowed with antitumor activity: Synthesis, biological evaluation and in silico insights. Int. J. Mol. Sci., 2019, 20(10), 2484.
[http://dx.doi.org/10.3390/ijms20102484] [PMID: 31137489]
[95]
Abo-Ashour, M.F.; Eldehna, W.M.; Nocentini, A.; Bonardi, A.; Bua, S.; Ibrahim, H.S.; Elaasser, M.M.; Kryštof, V.; Jorda, R.; Gratteri, P.; Abou-Seri, S.M.; Supuran, C.T. 3-Hydrazinoisatin-based benzenesulfonamides as novel carbonic anhydrase inhibitors endowed with anticancer activity: Synthesis, in vitro biological evaluation and in silico insights. Eur. J. Med. Chem., 2019, 184, 111768.
[http://dx.doi.org/10.1016/j.ejmech.2019.111768] [PMID: 31629164]
[96]
Alafeefy, A.M.; Ahmad, R.; Abdulla, M.; Eldehna, W.M.; Al-Tamimi, A-M.S.; Abdel-Aziz, H.A.; Al-Obaid, O.; Carta, F.; Al-Kahtani, A.A.; Supuran, C.T. Development of certain new 2-substituted-quinazolin-4-yl-aminobenzenesulfonamide as potential antitumor agents. Eur. J. Med. Chem., 2016, 109, 247-253.
[http://dx.doi.org/10.1016/j.ejmech.2016.01.001] [PMID: 26774930]
[97]
Eldehna, W.M.; Nocentini, A.; Al-Rashood, S.T.; Hassan, G.S.; Alkahtani, H.M.; Almehizia, A.A.; Reda, A.M.; Abdel-Aziz, H.A.; Supuran, C.T. Tumor-associated carbonic anhydrase isoform IX and XII inhibitory properties of certain isatin-bearing sulfonamides endowed with in vitro antitumor activity towards colon cancer. Bioorg. Chem., 2018, 81, 425-432.
[http://dx.doi.org/10.1016/j.bioorg.2018.09.007] [PMID: 30219719]
[98]
De Simone, G.; Supuran, C.T. Carbonic anhydrase IX: Biochemical and crystallographic characterization of a novel antitumor target. Biochim. Biophys. Acta, 2010, 1804(2), 404-409.
[http://dx.doi.org/10.1016/j.bbapap.2009.07.027] [PMID: 19679200]
[99]
Pastorek, J.; Pastorekova, S. Hypoxia-induced carbonic anhydrase IX as a target for cancer therapy: From biology to clinical use. Semin. Cancer Biol., 2015, 31, 52-64.
[http://dx.doi.org/10.1016/j.semcancer.2014.08.002] [PMID: 25117006]
[100]
Pastorekova, S.; Gillies, R.J. The role of carbonic anhydrase IX in cancer development: Links to hypoxia, acidosis, and beyond. Cancer Metastasis Rev., 2019, 38(1-2), 65-77.
[http://dx.doi.org/10.1007/s10555-019-09799-0] [PMID: 31076951]
[101]
Melis, C.; Distinto, S.; Bianco, G.; Meleddu, R.; Cottiglia, F.; Fois, B.; Taverna, D.; Angius, R.; Alcaro, S.; Ortuso, F.; Gaspari, M.; Angeli, A.; Del Prete, S.; Capasso, C.; Supuran, C.T.; Maccioni, E. Targeting tumor associated carbonic anhydrases IX and XII: Highly isozyme selective coumarin and psoralen inhibitors. ACS Med. Chem. Lett., 2018, 9(7), 725-729.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00170] [PMID: 30034608]
[102]
Lomelino, C.L.; Murray, A.B.; Supuran, C.T.; McKenna, R. Sweet binders: Carbonic anhydrase IX in complex with sucralose. ACS Med. Chem. Lett., 2018, 9(7), 657-661.
[http://dx.doi.org/10.1021/acsmedchemlett.8b00100] [PMID: 30034596]
[103]
Nocentini, A.; Lucidi, A.; Perut, F.; Massa, A.; Tomaselli, D.; Gratteri, P.; Baldini, N.; Rotili, D.; Mai, A.; Supuran, C.T. alpha, gamma-diketocarboxylic acids and their esters act as carbonic anhydrase IX and XII selective inhibitors. ACS Med. Chem. Lett., 2019, 10(4), 661-665.
[http://dx.doi.org/10.1021/acsmedchemlett.9b00023] [PMID: 30996814]
[104]
Aneja, B.; Khan, N.S.; Khan, P.; Queen, A.; Hussain, A.; Rehman, M.T.; Alajmi, M.F.; El-Seedi, H.R.; Ali, S.; Hassan, M.I.; Abid, M. Design and development of Isatin-triazole hydrazones as potential inhibitors of microtubule affinity-regulating kinase 4 for the therapeutic management of cell proliferation and metastasis. Eur. J. Med. Chem., 2019, 163, 840-852.
[http://dx.doi.org/10.1016/j.ejmech.2018.12.026] [PMID: 30579124]
[105]
Queen, A.; Khan, P.; Idrees, D.; Azam, A.; Hassan, M.I. Biological evaluation of p-toluene sulphonylhydrazone as carbonic anhydrase IX inhibitors: An approach to fight hypoxia-induced tumors. Int. J. Biol. Macromol., 2018, 106, 840-850.
[http://dx.doi.org/10.1016/j.ijbiomac.2017.08.082] [PMID: 28830777]
[106]
Gao, B.B.; Clermont, A.; Rook, S.; Fonda, S.J.; Srinivasan, V.J.; Wojtkowski, M.; Fujimoto, J.G.; Avery, R.L.; Arrigg, P.G.; Bursell, S.E.; Aiello, L.P.; Feener, E.P. Extracellular carbonic anhydrase mediates hemorrhagic retinal and cerebral vascular permeability through prekallikrein activation. Nat. Med., 2007, 13(2), 181-188.
[http://dx.doi.org/10.1038/nm1534] [PMID: 17259996]
[107]
Cholkar, K.; Trinh, H.M.; Pal, D.; Mitra, A.K. Discovery of novel inhibitors for the treatment of glaucoma. Expert Opin. Drug Discov., 2015, 10(3), 293-313.
[http://dx.doi.org/10.1517/17460441.2015.1000857] [PMID: 25575654]
[108]
Vadlapudi, A.D.; Patel, A.; Cholkar, K.; Mitra, A.K. Recent patents on emerging therapeutics for the treatment of glaucoma, age related macular degeneration and uveitis. Recent Pat. Biomed. Eng., 2012, 5(1), 83-101.
[http://dx.doi.org/10.2174/1874764711205010083] [PMID: 25414810]
[109]
Duan, Y.; Zhu, H. The advance in important target proteins. Curr. Top. Med. Chem., 2019, 19(15), 1275.
[http://dx.doi.org/10.2174/156802661915190827162456] [PMID: 31526338]
[110]
Liu, W.; Wang, X.; Zhu, H.; Duan, Y. Precision tumor medicine and drug targets. Curr. Top. Med. Chem., 2019, 19(17), 1488-1489.
[http://dx.doi.org/10.2174/156802661917190828111130] [PMID: 31592750]
[111]
Duan, Y.; Liu, W.; Tian, L.; Mao, Y.; Song, C. Targeting tubulin-colchicine site for cancer therapy: Inhibitors, antibody- drug conjugates and degradation agents. Curr. Top. Med. Chem., 2019, 19(15), 1289-1304.
[http://dx.doi.org/10.2174/1568026619666190618130008] [PMID: 31210108]
[112]
Duan, Y.T.; Sangani, C.B.; Liu, W.; Soni, K.V.; Yao, Y. New promises to cure cancer and other genetic diseases/disorders: Epi-drugs through epigenetics. Curr. Top. Med. Chem., 2019, 19(12), 972-994.
[http://dx.doi.org/10.2174/1568026619666190603094439] [PMID: 31161992]
[113]
Monti, S.M.; Supuran, C.T.; De Simone, G. Anticancer carbonic anhydrase inhibitors: A patent review (2008 - 2013). Expert Opin. Ther. Pat., 2013, 23(6), 737-749.
[http://dx.doi.org/10.1517/13543776.2013.798648] [PMID: 23672415]
[114]
Supuran, C.T. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites, 2017, 7(3), E48.
[http://dx.doi.org/10.3390/metabo7030048] [PMID: 28926956]
[115]
Supuran, C.T. Structure-based drug discovery of carbonic anhydrase inhibitors. J. Enzyme Inhib. Med. Chem., 2012, 27(6), 759-772.
[http://dx.doi.org/10.3109/14756366.2012.672983] [PMID: 22468747]
[116]
Supuran, C.T. Carbonic anhydrase inhibitors. Bioorg. Med. Chem. Lett., 2010, 20(12), 3467-3474.
[http://dx.doi.org/10.1016/j.bmcl.2010.05.009] [PMID: 20529676]
[117]
Winum, J.Y.; Scozzafava, A.; Montero, J.L.; Supuran, C.T. Design of zinc binding functions for carbonic anhydrase inhibitors. Curr. Pharm. Des., 2008, 14(7), 615-621.
[http://dx.doi.org/10.2174/138161208783877848] [PMID: 18336306]
[118]
Bozdag, M.; Ferraroni, M.; Nuti, E.; Vullo, D.; Rossello, A.; Carta, F.; Scozzafava, A.; Supuran, C.T. Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: Solution and X-ray crystallographic studies. Bioorg. Med. Chem., 2014, 22(1), 334-340.
[http://dx.doi.org/10.1016/j.bmc.2013.11.016] [PMID: 24300919]
[119]
Carta, F.; Supuran, C.T.; Scozzafava, A. Sulfonamides and their isosters as carbonic anhydrase inhibitors. Future Med. Chem., 2014, 6(10), 1149-1165.
[http://dx.doi.org/10.4155/fmc.14.68] [PMID: 25078135]
[120]
Fabrizi, F.; Mincione, F.; Somma, T.; Scozzafava, G.; Galassi, F.; Masini, E.; Impagnatiello, F.; Supuran, C.T. A new approach to antiglaucoma drugs: Carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J. Enzyme Inhib. Med. Chem., 2012, 27(1), 138-147.
[http://dx.doi.org/10.3109/14756366.2011.597749] [PMID: 21815773]
[121]
Thiry, A.; Dogné, J.M.; Supuran, C.T.; Masereel, B. Carbonic anhydrase inhibitors as anticonvulsant agents. Curr. Top. Med. Chem., 2007, 7(9), 855-864.
[http://dx.doi.org/10.2174/156802607780636726] [PMID: 17504130]
[122]
Abdel-Mohsen, H.T.; Ragab, F.A.F.; Ramla, M.M.; El Diwani, H.I. Novel benzimidazole-pyrimidine conjugates as potent antitumor agents. Eur. J. Med. Chem., 2010, 45(6), 2336-2344.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.011] [PMID: 20356655]
[123]
Alper Türkoğlu, E.; Şentürk, M.; Supuran, C.T.; Ekinci, D. Carbonic anhydrase inhibitory properties of some uracil derivatives. J. Enzyme Inhib. Med. Chem., 2017, 32(1), 74-77.
[http://dx.doi.org/10.1080/14756366.2016.1235043] [PMID: 28097897]
[124]
El-Azab, A.S.; Abdel-Aziz, A.A-M.; Bua, S.; Nocentini, A.; El-Gendy, M.A.; Mohamed, M.A.; Shawer, T.Z.; AlSaif, N.A.; Supuran, C.T. Synthesis of benzensulfonamides linked to quinazoline scaffolds as novel carbonic anhydrase inhibitors. Bioorg. Chem., 2019, 87, 78-90.
[http://dx.doi.org/10.1016/j.bioorg.2019.03.007] [PMID: 30878812]
[125]
Casini, A.; Mincione, F.; Vullo, D.; Menabuoni, L.; Scozzafava, A.; Supuran, C.T. Carbonic anhydrase inhibitors with strong topical antiglaucoma properties incorporating a 4-(2-aminopyrimidin-4-yl-amino)-benzenesulfonamide scaffold. J. Enzyme Inhib. Med. Chem., 2002, 17(1), 9-18.
[http://dx.doi.org/10.1080/14756360290018602] [PMID: 12365464]
[126]
Garibov, E.; Taslimi, P.; Sujayev, A.; Bingol, Z.; Çetinkaya, S.; Gulçin, İ.; Beydemir, S.; Farzaliyev, V.; Alwasel, S.H.; Supuran, C.T. Synthesis of 4,5-disubstituted-2-thioxo-1,2,3,4-tetrahydropyrimidines and investigation of their acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase I/II inhibitory and antioxidant activities. J. Enzyme Inhib. Med. Chem., 2016, 31(sup3), 1-9.
[http://dx.doi.org/10.1080/14756366.2016.1198901] [PMID: 27329935]
[127]
Domsic, J.F.; Avvaru, B.S.; Kim, C.U.; Gruner, S.M.; Agbandje-McKenna, M.; Silverman, D.N.; McKenna, R. Entrapment of carbon dioxide in the active site of carbonic anhydrase II. J. Biol. Chem., 2008, 283(45), 30766-30771.
[http://dx.doi.org/10.1074/jbc.M805353200] [PMID: 18768466]
[128]
Di Fiore, A.; Maresca, A.; Alterio, V.; Supuran, C.T.; De Simone, G. Carbonic anhydrase inhibitors: X-ray crystallographic studies for the binding of N-substituted benzenesulfonamides to human isoform II. Chem. Commun. (Camb.), 2011, 47(42), 11636-11638.
[http://dx.doi.org/10.1039/c1cc14575d] [PMID: 21952494]
[129]
El-Azab, A.S.; Abdel-Aziz, A.A.; Bua, S.; Nocentini, A.; AlSaif, N.A.; Alanazi, M.M.; El-Gendy, M.A.; Ahmed, H.E.A.; Supuran, C.T. S-substituted 2-mercaptoquinazolin-4(3H)-one and 4-ethylbenzensulfonamides act as potent and selective human carbonic anhydrase IX and XII inhibitors. J. Enzyme Inhib. Med. Chem., 2020, 35(1), 733-743.
[http://dx.doi.org/10.1080/14756366.2020.1742117] [PMID: 32189526]
[130]
Singh, P.; Swain, B.; Thacker, P.S.; Sigalapalli, D.K.; Purnachander Yadav, P.; Angeli, A.; Supuran, C.T.; Arifuddin, M. Synthesis and carbonic anhydrase inhibition studies of sulfonamide based indole-1,2,3-triazole chalcone hybrids. Bioorg. Chem., 2020, 99, 103839.
[http://dx.doi.org/10.1016/j.bioorg.2020.103839] [PMID: 32289586]
[131]
Grandane, A.; Nocentini, A.; Werner, T.; Zalubovskis, R.; Supuran, C.T. Benzoxepinones: A new isoform-selective class of tumor associated carbonic anhydrase inhibitors. Bioorg. Med. Chem., 2020, 28(11), 115496.
[http://dx.doi.org/10.1016/j.bmc.2020.115496] [PMID: 32327349]
[132]
Thacker, P.S.; Angeli, A.; Argulwar, O.S.; Tiwari, P.L.; Arifuddin, M.; Supuran, C.T. Design, synthesis and biological evaluation of coumarin linked 1,2,4-oxadiazoles as selective carbonic anhydrase IX and XII inhibitors. Bioorg. Chem., 2020, 98, 103739.
[http://dx.doi.org/10.1016/j.bioorg.2020.103739] [PMID: 32193032]
[133]
Aneja, B.; Queen, A.; Khan, P.; Shamsi, F.; Hussain, A.; Hasan, P.; Rizvi, M.M.A.; Daniliuc, C.G.; Alajmi, M.F.; Mohsin, M.; Hassan, M.I.; Abid, M. Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX. Bioorg. Med. Chem., 2020, 28(9), 115424.
[http://dx.doi.org/10.1016/j.bmc.2020.115424] [PMID: 32209296]
[134]
D’Ascenzio, M.; Secci, D.; Carradori, S.; Zara, S.; Guglielmi, P.; Cirilli, R.; Pierini, M.; Poli, G.; Tuccinardi, T.; Angeli, A.; Supuran, C.T. 1,3-dipolar cycloaddition, HPLC enantioseparation, and docking studies of saccharin/isoxazole and saccharin/isoxazoline derivatives as selective carbonic anhydrase IX and XII inhibitors. J. Med. Chem., 2020, 63(5), 2470-2488.
[http://dx.doi.org/10.1021/acs.jmedchem.9b01434] [PMID: 31972093]

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