{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,7]],"date-time":"2026-07-07T14:43:16Z","timestamp":1783435396996,"version":"3.54.6"},"reference-count":44,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2023,10,1]],"date-time":"2023-10-01T00:00:00Z","timestamp":1696118400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"published-print":{"date-parts":[[2023,10]]},"DOI":"10.1016\/j.bmcl.2023.129479","type":"journal-article","created":{"date-parts":[[2023,9,12]],"date-time":"2023-09-12T09:17:57Z","timestamp":1694510277000},"page":"129479","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":13,"special_numbering":"C","title":["Potent and selective carbonic anhydrase inhibition activities of pyrazolones bearing benzenesulfonamides"],"prefix":"10.1016","volume":"95","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4506-5265","authenticated-orcid":false,"given":"Suleyman","family":"Akocak","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nebih","family":"Lolak","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0669-7481","authenticated-orcid":false,"given":"Simone","family":"Giovannuzzi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4262-0323","authenticated-orcid":false,"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.bmcl.2023.129479_b0005","doi-asserted-by":"crossref","first-page":"4421","DOI":"10.1021\/cr200176r","article-title":"Multiple binding modes of inhibitors to carbonic anhydrases: how to design specific drugs targeting 15 different isoforms?","volume":"112","author":"Alterio","year":"2012","journal-title":"Chem Rev"},{"key":"10.1016\/j.bmcl.2023.129479_b0010","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":"10.1016\/j.bmcl.2023.129479_b0015","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1080\/17460441.2017.1253677","article-title":"Advances in structure-based drug discovery of carbonic anhydrase inhibitors","volume":"12","author":"Supuran","year":"2017","journal-title":"Expert Opin Drug Discov"},{"key":"10.1016\/j.bmcl.2023.129479_b0020","doi-asserted-by":"crossref","DOI":"10.1016\/j.bmcl.2023.129411","article-title":"A simple yet multifaceted 90 years old, evergreen enzyme: Carbonic anhydrase, its inhibition and activation","volume":"93","author":"Supuran","year":"2023","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2023.129479_b0025","doi-asserted-by":"crossref","unstructured":"Capasso C, Supuran CT. An overview of the alpha-, beta- and gamma-carbonic anhydrases from Bacteria: can bacterial carbonic anhydrases shed new light on evolution of bacteria? J Enzy Inhib Med Chem 2015; 30: 325\u2013332.","DOI":"10.3109\/14756366.2014.910202"},{"key":"10.1016\/j.bmcl.2023.129479_b0030","doi-asserted-by":"crossref","first-page":"1652","DOI":"10.1080\/14756366.2019.1664501","article-title":"Activation of \u03b1-, \u03b2-, \u03b3- \u03b4-, \u03b6- and \u03b7- class of carbonic anhydrases with amines and amino acids: a review","volume":"34","author":"Akocak","year":"2019","journal-title":"J Enzy Inhib Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0035","doi-asserted-by":"crossref","first-page":"345","DOI":"10.3109\/14756366.2015.1122001","article-title":"How many carbonic anhydrase inhibition mechanisms exist?","volume":"31","author":"Supuran","year":"2016","journal-title":"J Enzym Inhib Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0040","doi-asserted-by":"crossref","first-page":"5077","DOI":"10.1021\/acs.jmedchem.6b00492","article-title":"PEGylated bis-sulfonamide carbonic anhydrase inhibitors can efficiently control the growth of several carbonic anhydrase ix-expressing carcinomas","volume":"59","author":"Akocak","year":"2016","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0045","doi-asserted-by":"crossref","first-page":"17792","DOI":"10.1021\/acsami.8b05607","article-title":"pH-Senstive multiligand gold nanoplatform targeting carbonic anhydrase IX enhances the delivery of Doxorubicin to hypoxic tumor spheroids and overcomes the hypoxia-induced chemoresistance","volume":"10","author":"Shabana","year":"2018","journal-title":"ACS Appl Mater Interfaces"},{"key":"10.1016\/j.bmcl.2023.129479_b0050","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1080\/13543776.2018.1523897","article-title":"Carbonic anhydrase inhibitors and their potential in a range of therapeutic areas","volume":"28","author":"Supuran","year":"2018","journal-title":"Expert Opin Ther Pat"},{"key":"10.1016\/j.bmcl.2023.129479_b0055","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1080\/13543776.2019.1629419","article-title":"Carbonic anhydrase as disease markers","volume":"29","author":"Zamanova","year":"2019","journal-title":"Expert Opin Ther Targets"},{"key":"10.1016\/j.bmcl.2023.129479_b0060","doi-asserted-by":"crossref","first-page":"1215","DOI":"10.1080\/14756366.2020.1765166","article-title":"Synthesis of calix [4] azacrown substituted sulphonamides with antioxidant, acetylcholinesterase, butyrylcholinesterase, tyrosinase and carbonic anhydrase inhibitory action","volume":"35","author":"Oguz","year":"2020","journal-title":"J. Enzy. Inhib. Med. Chem."},{"key":"10.1016\/j.bmcl.2023.129479_b0065","doi-asserted-by":"crossref","first-page":"729","DOI":"10.1080\/13543776.2018.1508453","article-title":"Carbonic anhydrase inhibitors as antitumor\/antimetastatic agents: a patent review (2008\u20132018)","volume":"28","author":"Nocentini","year":"2018","journal-title":"Expert Opin Ther Pat"},{"key":"10.1016\/j.bmcl.2023.129479_b0070","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":"10.1016\/j.bmcl.2023.129479_b0075","doi-asserted-by":"crossref","first-page":"25","DOI":"10.3390\/metabo8020025","article-title":"Carbonic anhydrases and metabolism","volume":"8","author":"Supuran","year":"2018","journal-title":"Metabolites"},{"key":"10.1016\/j.bmcl.2023.129479_b0080","doi-asserted-by":"crossref","first-page":"3364","DOI":"10.1158\/0008-5472.CAN-10-4261","article-title":"Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors","volume":"71","author":"Lou","year":"2011","journal-title":"Cancer Res"},{"key":"10.1016\/j.bmcl.2023.129479_b0085","doi-asserted-by":"crossref","first-page":"8371","DOI":"10.1039\/c0cc02707c","article-title":"Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency","volume":"46","author":"Pacchiano","year":"2010","journal-title":"Chem Commun (Camb)"},{"key":"10.1016\/j.bmcl.2023.129479_b0090","doi-asserted-by":"crossref","first-page":"1896","DOI":"10.1021\/jm101541x","article-title":"Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis","volume":"54","author":"Pacchiano","year":"2011","journal-title":"J Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0095","doi-asserted-by":"crossref","first-page":"4566","DOI":"10.1016\/j.ejmech.2011.07.035","article-title":"Design and synthesis of some new thiophene, thienopyrimidine and thienothiadiazine derivatives of antipyrine as potential antimicrobial agents","volume":"46","author":"Aly","year":"2011","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0100","doi-asserted-by":"crossref","first-page":"149","DOI":"10.2174\/1570180812666150630182740","article-title":"Design and synthesis of novel spiro-piperidinyl pyrazolone derivatives and their potential antiviral activity","volume":"13","author":"Srinivasan","year":"2016","journal-title":"Lett Drug Des Discov"},{"key":"10.1016\/j.bmcl.2023.129479_b0105","doi-asserted-by":"crossref","first-page":"3035","DOI":"10.1016\/j.bmc.2016.05.013","article-title":"Identification, synthesis and evaluation of SARS-CoV and MERS-CoV 3C-like protease inhibitors","volume":"24","author":"Kumar","year":"2016","journal-title":"Bioorg Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0110","doi-asserted-by":"crossref","DOI":"10.1016\/j.molstruc.2021.130665","article-title":"Design and synthesis of pyrazolone-based compounds as potent blockers of SARS-CoV-2 viral entry into the host cells","volume":"1241","author":"Obakachi","year":"2021","journal-title":"J Mol Struct"},{"key":"10.1016\/j.bmcl.2023.129479_b0115","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1007\/s00044-013-0636-y","article-title":"Synthesis, evaluation and docking studies on steroidal pyrazolones as anticancer and antimicrobial agents","volume":"23","author":"Shamsuzzaman","year":"2014","journal-title":"Med Chem Res"},{"key":"10.1016\/j.bmcl.2023.129479_b0120","doi-asserted-by":"crossref","first-page":"620","DOI":"10.1111\/cbdd.14030","article-title":"1,3-diarylpyrazolones as potential anticancer agents for non-small cell lung cancer: Synthesis and antiproliferative activity evaluation","volume":"99","author":"Dahal","year":"2022","journal-title":"Chem Biol Drug Des"},{"key":"10.1016\/j.bmcl.2023.129479_b0125","doi-asserted-by":"crossref","first-page":"558","DOI":"10.3329\/bjp.v11i2.25859","article-title":"Synthesis and anti-depressant evaluation of novel pyrazolone derivatives","volume":"11","author":"Merugumolu","year":"2016","journal-title":"Bangladesh J Pharmacol"},{"key":"10.1016\/j.bmcl.2023.129479_b0130","doi-asserted-by":"crossref","first-page":"952","DOI":"10.1016\/j.bmcl.2018.01.043","article-title":"Design, synthesis, anti-inflammatory activity and molecular docking of potential novel antipyrine and pyrazolone analogs as cyclooxygenase enzyme (COX) inhibitors","volume":"28","author":"El Sayed","year":"2018","journal-title":"Bioorg Med Chem Lett"},{"key":"10.1016\/j.bmcl.2023.129479_b0135","doi-asserted-by":"crossref","first-page":"784","DOI":"10.1111\/cbdd.12712","article-title":"Synthesis of novel substituted thiourea and benzimidazole derivatives containing a pyrazolone ring as anti-inflammatory agents","volume":"87","author":"Moneer","year":"2016","journal-title":"Chem Biol Drug Des"},{"key":"10.1016\/j.bmcl.2023.129479_b0140","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.bioorg.2018.03.011","article-title":"Design, synthesis, analgesic, anti-inflammatory activity of novel pyrazolones possessing aminosulfonyl pharmacophore as inhibitors of COX-2\/5-LOX enzymes: Histopathological and docking studies","volume":"78","author":"Abdelgawad","year":"2018","journal-title":"Bioorg Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0145","first-page":"802","article-title":"Synthesis of 4-amino-1,5-dimethyl-2 phenylpyrazolone derivatives and their antioxidant activity","volume":"37","author":"Khan","year":"2015","journal-title":"J Chem Soc Pakistan"},{"key":"10.1016\/j.bmcl.2023.129479_b0150","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1002\/jhet.2588","article-title":"Synthesis and antioxidant activity of some new thiazolyl-pyrazolone derivatives","volume":"54","author":"Gaffer","year":"2017","journal-title":"J Heterocycl Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0155","doi-asserted-by":"crossref","first-page":"2884","DOI":"10.1039\/D2RA08280B","article-title":"Pyrazolone-type compounds (part II): in vitro and in silico evaluation of antioxidant potential; structure\u2013activity relationship","volume":"13","author":"Brankovic","year":"2023","journal-title":"RSC Adv"},{"key":"10.1016\/j.bmcl.2023.129479_b0160","doi-asserted-by":"crossref","first-page":"94786","DOI":"10.1039\/C5RA17391D","article-title":"Design, synthesis, anticonvulsant and analgesic studies of new pyrazole analogues: a Knoevenagel reaction approach","volume":"5","author":"Viveka","year":"2015","journal-title":"RSC Adv"},{"key":"10.1016\/j.bmcl.2023.129479_b0165","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2019.111893","article-title":"Pyrazolone structural motif in medicinal chemistry: Retrospect and prospect","volume":"186","author":"Zhao","year":"2020","journal-title":"Eur J Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0170","doi-asserted-by":"crossref","first-page":"1575","DOI":"10.1080\/14756366.2018.1515933","article-title":"Discovery of novel 1,3-diaryltriazene sulfonamides as carbonic anhydrase I, II, VII and IX inhibitors","volume":"33","author":"Akocak","year":"2018","journal-title":"J Enzy Inhib Med Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0175","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1016\/j.bioorg.2018.01.022","article-title":"Synthesis and biological evaluation of novel N, N\u2019-diaryl cyanoguanidines acting as potent and selective carbonic anhydrase II inhibitors","volume":"77","author":"Akocak","year":"2018","journal-title":"Bioorg Chem"},{"key":"10.1016\/j.bmcl.2023.129479_b0180","doi-asserted-by":"crossref","first-page":"3093","DOI":"10.1016\/j.bmc.2017.03.063","article-title":"Synthesis and biological evaluation of novel aromatic and heterocyclic bis-sulfonamide Schiff bases as carbonic anhydrase I, II, VII and IX inhibitors","volume":"25","author":"Akocak","year":"2017","journal-title":"Bioorg Med Chem"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0185.1","doi-asserted-by":"crossref","unstructured":"(a) Lolak N, Akocak S, Bua S, Koca M, Supuran CT. Design and synthesis of novel 1,3-diaryltriazene-substituted sulfonamides as potent and selective carbonic anhydrase II inhibitors. Bioorg. Chem. 2018","DOI":"10.1016\/j.bioorg.2018.02.015"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0185.2","doi-asserted-by":"crossref","unstructured":"c) Akocak S, Lolak N, Duran HE, et al. Synthesis and Characterization of Novel 1,3-Diaryltriazene-Substituted Sulfaguanidine Derivatives as Selective Carbonic Anhydrase Inhibitors: Biological Evaluation, in Silico ADME\/T and Molecular Docking Study. Chem. Biodivers. 2023","DOI":"10.21203\/rs.3.rs-2812331\/v1"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0185.3","doi-asserted-by":"crossref","unstructured":"(a) Lolak N, Akocak S, Bua S, Koca M, Supuran CT. Design and synthesis of novel 1,3-diaryltriazene-substituted sulfonamides as potent and selective carbonic anhydrase II inhibitors. Bioorg. Chem. 2018; 77: 542-547;","DOI":"10.1016\/j.bioorg.2018.02.015"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0185.4","doi-asserted-by":"crossref","unstructured":"(b) Is\u0131k M, Akocak S, Lolak N, et al. Synthesis, characterization, biological evaluation, and in silico studies of novel 1, 3\u2010diaryltriazene\u2010substituted sulfathiazole derivatives. Arch. Pharm. 2020; 353(9): 2000102; c) Akocak S, Lolak N, Duran HE, et al. Synthesis and Characterization of Novel 1,3-Diaryltriazene-Substituted Sulfaguanidine Derivatives as Selective Carbonic Anhydrase Inhibitors: Biological Evaluation, in Silico ADME\/T and Molecular Docking Study. Chem. Biodivers. 2023; 20: e202300611.","DOI":"10.1002\/cbdv.202300611"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0190.1","doi-asserted-by":"crossref","unstructured":"(a) Lolak N, Akocak S, Bua S, Supuran CT. Design, synthesis and biological evaluation of novel ureido benzenesulfonamides incorporating 1,3,5-triazine moieties as potent carbonic anhydrase IX inhibitors. Bioorg. Chem. 2019","DOI":"10.1016\/j.bioorg.2018.10.005"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0190.2","doi-asserted-by":"crossref","unstructured":"(b) Lolak N, Akocak S, Bua S, Sanku RKK, Supuran CT. Discovery of new ureido benzenesulfonamides incorporating 1, 3, 5-triazine moieties as carbonic anhydrase I, II, IX and XII inhibitors. Bioorg. Med. Chem. 2019","DOI":"10.1016\/j.bioorg.2018.10.005"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0190.3","doi-asserted-by":"crossref","unstructured":"(a) Lolak N, Akocak S, Bua S, Supuran CT. Design, synthesis and biological evaluation of novel ureido benzenesulfonamides incorporating 1,3,5-triazine moieties as potent carbonic anhydrase IX inhibitors. Bioorg. Chem. 2019; 82: 117-122;","DOI":"10.1016\/j.bioorg.2018.10.005"},{"key":"#cr-split#-10.1016\/j.bmcl.2023.129479_b0190.4","doi-asserted-by":"crossref","unstructured":"(b) Lolak N, Akocak S, Bua S, Sanku RKK, Supuran CT. Discovery of new ureido benzenesulfonamides incorporating 1, 3, 5-triazine moieties as carbonic anhydrase I, II, IX and XII inhibitors. Bioorg. Med. Chem. 2019; 27(8): 1588-1594.","DOI":"10.1016\/j.bmc.2019.03.001"}],"container-title":["Bioorganic &amp; Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X23003578?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X23003578?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:49:06Z","timestamp":1760773746000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X23003578"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,10]]},"references-count":44,"alternative-id":["S0960894X23003578"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2023.129479","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2023,10]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Potent and selective carbonic anhydrase inhibition activities of pyrazolones bearing benzenesulfonamides","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2023.129479","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2023 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"129479"}}