{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T14:33:08Z","timestamp":1791469988975,"version":"4.3.4"},"reference-count":82,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2022,2,28]],"date-time":"2022-02-28T00:00:00Z","timestamp":1646006400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Coumarin is an important six-membered aromatic heterocyclic pharmacophore, widely distributed in natural products and synthetic molecules. The versatile and unique features of coumarin nucleus, in combination with privileged sulfonamide moiety, have enhanced the broad spectrum of biological activities. The research and development of coumarin, sulfonamide-based pharmacology, and medicinal chemistry have become active topics, and attracted the attention of medicinal chemists, pharmacists, and synthetic chemists. Coumarin sulfonamide compounds and analogs as clinical drugs have been used to cure various diseases with high therapeutic potency, which have shown their enormous development value. The diversified and wide array of biological activities such as anticancer, antibacterial, anti-fungal, antioxidant and anti-viral, etc. were displayed by diversified coumarin sulfonamides. The present systematic and comprehensive review in the current developments of synthesis and the medicinal chemistry of coumarin sulfonamide-based scaffolds give a whole range of therapeutics, especially in the field of oncology and carbonic anhydrase inhibitors. In the present review, various synthetic approaches, strategies, and methodologies involving effect of catalysts, the change of substrates, and the employment of various synthetic reaction conditions to obtain high yields is cited.<\/jats:p>","DOI":"10.3390\/molecules27051604","type":"journal-article","created":{"date-parts":[[2022,2,28]],"date-time":"2022-02-28T20:11:14Z","timestamp":1646079074000},"page":"1604","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":52,"title":["An Update on Synthesis of Coumarin Sulfonamides as Enzyme Inhibitors and Anticancer Agents"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8225-4925","authenticated-orcid":false,"given":"Laila","family":"Rubab","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Lahore, Sargodha Campus, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sumbal","family":"Afroz","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Government College University Lahore, Lahore 54000, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sajjad","family":"Ahmad","sequence":"additional","affiliation":[{"name":"Department of Chemistry, UET Lahore, Faisalabad Campus, Faisalabad 37630, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saddam","family":"Hussain","sequence":"additional","affiliation":[{"name":"School of Biochemistry, Minhaj University Lahore, Lahore 54590, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iram","family":"Nawaz","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Lahore, Sargodha Campus, Sargodha 40100, Pakistan"},{"name":"Abdul Razzaq Fazaia College, M.M. Alam Base Mianwali, Mainwali 42206, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8977-3303","authenticated-orcid":false,"given":"Ali","family":"Irfan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Government College University Faisalabad, 5-Km, Jhang Road, Faisalabad 38040, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fozia","family":"Batool","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Lahore, Sargodha Campus, Sargodha 40100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katarzyna","family":"Kotwica-Mojzych","sequence":"additional","affiliation":[{"name":"Department of Histology, Embryology and Cytophysiology, Medical University of Lublin, Radziwi\u0142\u0142owska 11, 20-080 Lublin, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9884-6068","authenticated-orcid":false,"given":"Mariusz","family":"Mojzych","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Siedlce University of Natural Sciences and Humanities, 3-go Maja 54, 08-110 Siedlce, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,2,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.cbi.2016.05.001","article-title":"Coumarins as cholinesterase inhibitors. A review","volume":"254","year":"2016","journal-title":"Chem. Biol. Interact."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3884","DOI":"10.2174\/1381612811319210013","article-title":"Current developments of coumarin compounds in medicinal chemistry","volume":"19","author":"Peng","year":"2013","journal-title":"Curr. Pharm. Des."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"365","DOI":"10.2174\/138955706776361457","article-title":"Synthetic and natural coumarins as antioxidants","volume":"6","author":"Kostova","year":"2006","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"124","DOI":"10.2174\/1568026618666180329115523","article-title":"Coumarin compounds in medicinal chemistry: Some important examples from the last years","volume":"18","author":"Pereira","year":"2018","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1039\/np9951200477","article-title":"Coumarins","volume":"12","author":"Murray","year":"1995","journal-title":"Nat. Prod. Rep."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"8846","DOI":"10.1039\/C6NJ01532H","article-title":"Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes","volume":"40","author":"Pereira","year":"2016","journal-title":"New J. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1139","DOI":"10.1016\/j.bmcl.2008.12.098","article-title":"Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors","volume":"19","author":"Symeonidis","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7205","DOI":"10.1016\/j.bmcl.2010.10.116","article-title":"Synthesis and in vitro evaluation of novel coumarinechalcone hybrids as potential anticancer agents","volume":"20","author":"Sashidhara","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4093","DOI":"10.1016\/j.bmcl.2004.05.016","article-title":"Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity","volume":"14","author":"Reddy","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/j.ejmech.2014.02.026","article-title":"Youns, Anticancer activity of new coumarin substituted hydrazide-hydrazone derivatives","volume":"76","author":"Nasr","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1016\/j.ejmech.2015.07.010","article-title":"Coumarins as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies","volume":"101","author":"Thakur","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"5770","DOI":"10.1016\/j.bmcl.2011.08.005","article-title":"Pancreatic anticancer activity of a novel geranylgeranylatedcoumarin derivative","volume":"21","author":"Devji","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Alshibl, H.M., Al-Abdullah, E.S., Haiba, M.E., Alkahtani, H.M., Awad, G.E.A., Mahmoud, A.H., Ibrahim, B.M.M., Bari, A., and Villinger, A. (2020). Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents. Molecules, 25.","DOI":"10.3390\/molecules25143251"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3020","DOI":"10.1016\/j.ejmech.2008.12.027","article-title":"Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts","volume":"44","author":"Melagraki","year":"2009","journal-title":"Eur. J. Med. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3813","DOI":"10.2174\/1381612043382710","article-title":"Natural and synthetic coumarin derivatives with anti-inflammatory\/antioxidant activities","volume":"10","author":"Fylaktakidou","year":"2004","journal-title":"Curr. Pharm. Des."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1080\/1475636031000069291","article-title":"Biological evaluation of several coumarins derivatives designed as possible anti-inflammatory\/antioxidant agents","volume":"18","author":"Kontogiorgis","year":"2003","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1080\/14756360500141911","article-title":"In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes","volume":"20","author":"Rehman","year":"2005","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_18","first-page":"263","article-title":"Synthesis and biological activity of 6-substituted-3-[2-(5-substituted-2-furfurylidenehydrazino)-4-thiazolyl] coumarins","volume":"139","author":"Kalluraya","year":"2000","journal-title":"Boll. Chim. Farm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1695","DOI":"10.1016\/S0960-894X(00)00304-8","article-title":"Improved antibacterial activities of coumarin antibiotics bearing 5\u2032,5\u2032-dialkylnoviose: Biological activity of RU79115","volume":"10","author":"Musiciki","year":"2000","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_20","first-page":"693","article-title":"Antibacterial activity of coumarins","volume":"60","author":"Monache","year":"2005","journal-title":"Z. Nat. C"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"925096","DOI":"10.1155\/2015\/925096","article-title":"Evaluation of antifungal activity and mode of action of new coumarin derivative, 7-hydroxy-6-nitro-2h-1-benzopyran-2-one, against Aspergillus spp.","volume":"2015","author":"Guerra","year":"2015","journal-title":"Evid. Based Complement. Altern. Med."},{"key":"ref_22","first-page":"21","article-title":"Antifungal activity of coumarins","volume":"63","author":"Montagner","year":"2008","journal-title":"Z. Nat. C J. Biosci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1933","DOI":"10.1016\/S0968-0896(99)00138-8","article-title":"Synthesis and antifungal activity of coumarins and angular furanocoumarins","volume":"7","author":"Sardari","year":"1999","journal-title":"Bioorg. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1016\/S0223-5234(03)00016-3","article-title":"Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents","volume":"38","author":"Ghate","year":"2003","journal-title":"Eur. J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6400","DOI":"10.1021\/jm0580149","article-title":"Synthesis and anti-inflammatory activity of coumarin derivatives","volume":"48","author":"Christos","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1253","DOI":"10.1111\/jphp.12774","article-title":"Coumarins as potential antidiabetic agents","volume":"69","author":"Li","year":"2017","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1016\/S0960-894X(02)00015-X","article-title":"Synthesis and vasorelaxant activity of new coumarin and furocoumarin derivatives","volume":"12","author":"Orallo","year":"2002","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"882","DOI":"10.1016\/j.ejmech.2005.03.025","article-title":"Synthesis and in vivo analgesic and anti-inflammatory activity of some bi heterocyclic coumarin derivatives","volume":"40","author":"Ghate","year":"2005","journal-title":"Eur. J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"68274","DOI":"10.1155\/BCA\/2006\/68274","article-title":"Structure-activity relationships of synthetic coumarins as hiv-1 inhibitors","volume":"2006","author":"Kostova","year":"2006","journal-title":"Bioinorg. Chem. Appl."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1016\/S0378-8741(00)00279-8","article-title":"Antimicrobial activity of some coumarin containing herbal plants growing in Finland","volume":"73","author":"Ojala","year":"2000","journal-title":"J. Ethnopharmacol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3371","DOI":"10.1016\/j.bmc.2010.04.009","article-title":"Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives","volume":"18","author":"Abdelhafez","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_32","first-page":"253","article-title":"Evaluation of antipyretic and antinociceptive potential of new heterocyclic derivatives of 3-formyl-4-hydroxycoumarin in rats","volume":"3","author":"Ahmad","year":"2013","journal-title":"J. Pharm. Appl. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s11094-018-1756-y","article-title":"Solvent-free synthesis and antibacterial evaluation of novel coumarin sulfonamides","volume":"52","author":"Mostajeran","year":"2018","journal-title":"Pharm. Chem. J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1515\/hc-2020-0008","article-title":"Coumarin sulfonamide derivatives: An emerging class of therapeutic agents","volume":"26","author":"Irfan","year":"2020","journal-title":"Heterocycl. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"8329","DOI":"10.1021\/ja061574s","article-title":"Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX","volume":"128","author":"Alterio","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3975","DOI":"10.1021\/acs.jmedchem.5b00523","article-title":"Substituted sulfocoumarins are selectivecarbonic anhdydrase IX and XII inhibitors with significant cytotoxicity against colorectal cancer cells","volume":"58","author":"Grandane","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/j.jcrpr.2017.07.001","article-title":"Review of cancer from perspective of molecular","volume":"4","author":"Hassanpour","year":"2017","journal-title":"J. Cancer Res. Pract."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3279","DOI":"10.3390\/cancers3033279","article-title":"Assessment of the evolution of cancer treatment therapies","volume":"3","author":"Arruebo","year":"2011","journal-title":"Cancers"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1038\/nature11125","article-title":"The mutational landscape of lethal castration-resistant prostate cancer","volume":"487","author":"Grasso","year":"2012","journal-title":"Nature"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"759","DOI":"10.3109\/14756366.2012.672983","article-title":"Structure-based drug discovery of carbonic anhydrase inhibitors","volume":"27","author":"Supuran","year":"2012","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4873","DOI":"10.1016\/j.bmc.2010.06.028","article-title":"Coumarinyl-substituted sulfonamides strongly inhibit several human carbonic anhydrase isoforms: Solution and crystallographic investigations","volume":"18","author":"Wagner","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"34","DOI":"10.3389\/fphar.2011.00034","article-title":"Bacterial carbonic anhydrases as drug targets: Toward novel antibiotics","volume":"2","author":"Supuran","year":"2011","journal-title":"Front. Pharmacol."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1038\/nrd3554","article-title":"Interfering with pH regulation in tumours as a therapeutic strategy","volume":"10","author":"Neri","year":"2011","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1517\/13543776.2013.778246","article-title":"Carbonic anhydrase inhibitors: An editorial","volume":"23","author":"Supuran","year":"2013","journal-title":"Expert Opin. Ther. Pat."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Angeli, A., Carta, F., and Supuran, C.T. (2020). Carbonic Anhydrases: Versatile and Useful Biocatalysts in Chemistry and Biochemistry. Catalysts, 10.","DOI":"10.3390\/catal10091008"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"325","DOI":"10.3109\/14756366.2014.910202","article-title":"An overview of the alpha-, beta- and gamma-carbonic anhydrases from bacteria: Can bacterial carbonic anhydrases shed new light on evolution of bacteria","volume":"30","author":"Capasso","year":"2015","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1517\/14728222.2014.991312","article-title":"The \u03b7-class carbonic anhydrases as drug targets for antimalarial agents","volume":"19","author":"Supuran","year":"2015","journal-title":"Expert Opin. Ther. Targets"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"906","DOI":"10.3109\/14756366.2013.868599","article-title":"Biochemical characterization of the \u03b4-carbonic anhydrase from the marine diatom Thalassiosiraweissflogii, TweCA","volume":"29","author":"Vullo","year":"2014","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1080\/14756366.2018.1468530","article-title":"Activation of \u03b2- and \u03b3-carbonic anhydrases from pathogenic bacteria with tripeptides","volume":"33","author":"Stefanucci","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1016\/j.bioorg.2018.06.002","article-title":"The first activation studies of the \u03b7-carbonic anhydrase from the malaria parasite Plasmodium falciparum with amines and amino acids","volume":"80","author":"Angeli","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1016\/j.bioorg.2018.05.027","article-title":"The zinc\u2014But not cadmium\u2014Containing \u03b6-carbonic from the diatom Thalassiosiraweissflogii is potently activated by amines and amino acids","volume":"80","author":"Angeli","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"4187","DOI":"10.1016\/j.bmc.2018.07.011","article-title":"Activation studies with amines and amino acids of the \u03b1-carbonic anhydrase from the pathogenic protozoan Trypanosoma cruzi","volume":"26","author":"Angeli","year":"2018","journal-title":"Bioorg. Med. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"364","DOI":"10.1080\/14756366.2017.1422250","article-title":"Activation studies with amines and amino acids of the \u03b2-carbonic anhydrase encoded by the Rv3273 gene from the pathogenic bacterium Mycobacterium tuberculosis","volume":"33","author":"Angeli","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bioorg.2018.01.003","article-title":"The \u03b3-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae is potently activated by amines and amino acids","volume":"77","author":"Angeli","year":"2018","journal-title":"Bioorg. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2094","DOI":"10.1038\/s41396-019-0426-8","article-title":"A new widespread subclass of carbonic anhydrase in marine phytoplankton","volume":"13","author":"Jensen","year":"2019","journal-title":"ISME J."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"7229","DOI":"10.1016\/j.bmc.2007.08.037","article-title":"Carbonic anhydrase inhibitors: Cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides","volume":"15","author":"Nishimori","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"7697","DOI":"10.1002\/anie.200701189","article-title":"Saccharin inhibits carbonicanhydrases: Possible explanation for its unpleasant metallic aftertaste","volume":"46","author":"Hillebrecht","year":"2007","journal-title":"Angew. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"381","DOI":"10.1080\/14756360009040695","article-title":"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","volume":"15","author":"Supuran","year":"2000","journal-title":"J. Enzym. Inhib."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1021\/jm990479+","article-title":"Carbonic anhydrase inhibitors. Synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus the cytosolic isozymes","volume":"43","author":"Scozzafava","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"5544","DOI":"10.1021\/jm060531j","article-title":"Carbonic anhydrase inhibitors:hypoxia-activatable sulfonamides incorporatingdisulfide bonds that target the tumor-associatedisoform IX","volume":"49","author":"Vitale","year":"2006","journal-title":"J. Med. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/ja809683v","article-title":"Non-zinc mediated inhibition of carbonic anhydrases: Coumarins are a new class of suicide inhibitors","volume":"131","author":"Maresca","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1021\/jm901287j","article-title":"Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins","volume":"53","author":"Maresca","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1038\/nrd2467","article-title":"Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators","volume":"7","author":"Supuran","year":"2008","journal-title":"Nat. Rev. Drug. Discov."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2023","DOI":"10.1042\/BCJ20160115","article-title":"Structure and function of carbonic anhydrases","volume":"473","author":"Supuran","year":"2016","journal-title":"Biochem. J."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1175","DOI":"10.1080\/17460441.2019.1651289","article-title":"Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery","volume":"14","author":"Nocentini","year":"2019","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1462","DOI":"10.1080\/14756366.2020.1788009","article-title":"Coumarin carbonic anhydrase inhibitors from natural sources","volume":"35","author":"Supuran","year":"2020","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ejmech.2013.04.035","article-title":"Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis","volume":"66","author":"Wang","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"78","DOI":"10.3109\/14756366.2015.1077823","article-title":"Synthesis, antioxidant and carbonic anhydrase I and II inhibitory activities of novel sulphonamide-substituted coumarylthiazole derivatives","volume":"31","author":"Kurt","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"9152","DOI":"10.1021\/jm501314c","article-title":"Structural insights on carbonic anhydrase inhibitory action, isoform selectivity, and potency of sulfonamides and coumarins incorporating arylsulfonylureido groups","volume":"57","author":"Bozdag","year":"2014","journal-title":"J. Med. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"2882","DOI":"10.1016\/j.bmc.2016.04.052","article-title":"Novel sulfonamide bearing coumarin scaffolds as selective inhibitors of tumor associated carbonic anhydrase isoforms IX and XII","volume":"24","author":"Chandak","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"3491","DOI":"10.1016\/j.bmcl.2016.06.037","article-title":"Coumarin sulfonamides derivatives as potent and selective COX-2 inhibitors with efficacy in suppressing cancer proliferation and metastasis","volume":"26","author":"Lu","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"113589","DOI":"10.1016\/j.ejmech.2021.113589","article-title":"Investigation of 3-sulfamoyl coumarins against cancer-related IX and XII isoforms of human carbonic anhydrase as well as cancer cells leads to the discovery of 2-oxo-2H-benzo[h]chromene-3-sulfonamide. A new caspase-activating proapoptotic agent","volume":"222","author":"Kantin","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"111702","DOI":"10.1016\/j.ejmech.2019.111702","article-title":"Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies","volume":"183","author":"Zengin","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"112897","DOI":"10.1016\/j.ejmech.2020.112897","article-title":"Novel 3-substituted coumarins as selective human carbonic anhydrase IX and XII inhibitors: Synthesis, biological and molecular dynamics analysis","volume":"209","author":"Abdelrahman","year":"2021","journal-title":"Eur. J. Med. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"6223","DOI":"10.1016\/j.bmcl.2013.10.001","article-title":"The sulfamide moiety affords higher inhibitory activity and oral bioavailability to a series of coumarin dual selective RAF\/MEK inhibitors","volume":"23","author":"Aoki","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/j.ejmech.2012.12.004","article-title":"Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents","volume":"60","author":"Amin","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","unstructured":"Zhang, J., Tan, Y., Li, G., Chen, L., Nie, M., Wang, Z., and Ji, H. (2021). Coumarin Sulfonamides and Amides Derivatives: Design, Synthesis, and Antitumor Activity In Vitro. Molecules, 26.","DOI":"10.3390\/molecules26040786"},{"key":"ref_78","first-page":"49","article-title":"Synthesis and molecular docking of novel non-cytotoxic anti-angiogenic sulfonyl coumarin derivatives against hepatocellular carcinoma cells in vitro","volume":"7","author":"Ebaid","year":"2017","journal-title":"J. Appl. Pharm. Sci."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"4638","DOI":"10.1002\/slct.201600665","article-title":"Design, Synthesis and Structure-Activity Relationship Study of Coumarin Benzimidazole Hybrid as Potent Antibacterial and Anticancer Agents","volume":"1","author":"Holiyachi","year":"2016","journal-title":"ChemistrySelect"},{"key":"ref_80","first-page":"2869","article-title":"Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents","volume":"49","author":"Durgapal","year":"2019","journal-title":"Synth. Commun."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1080\/14756366.2018.1477137","article-title":"ANovel coumarin-6-sulfonamides as apoptotic anti-proliferative agents: Synthesis, in vitro biological evaluation, and QSAR studies","volume":"33","author":"Sabt","year":"2018","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1080\/14756366.2016.1217851","article-title":"Study of reactivity of cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide: Preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase","volume":"31","author":"Debbabi","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/5\/1604\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:29:30Z","timestamp":1760135370000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/5\/1604"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,2,28]]},"references-count":82,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2022,3]]}},"alternative-id":["molecules27051604"],"URL":"https:\/\/doi.org\/10.3390\/molecules27051604","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,2,28]]}}}