{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T23:34:08Z","timestamp":1788910448371,"version":"build-2803163510"},"reference-count":31,"publisher":"Elsevier BV","content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2014,1]]},"DOI":"10.1016\/j.ejmech.2013.10.081","type":"journal-article","created":{"date-parts":[[2013,11,10]],"date-time":"2013-11-10T14:49:46Z","timestamp":1384094986000},"page":"135-147","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":65,"special_numbering":"C","title":["Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N\u2032-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII"],"prefix":"10.1016","volume":"71","author":[{"given":"Beata","family":"\u017bo\u0142nowska","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaros\u0142aw","family":"S\u0142awi\u0144ski","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aneta","family":"Pogorzelska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaros\u0142aw","family":"Chojnacki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniela","family":"Vullo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudiu T.","family":"Supuran","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2013.10.081_bib1","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1002\/med.10025","article-title":"Carbonic anhydrase inhibitors","volume":"23","author":"Supuran","year":"2003","journal-title":"Med. Res. Rev."},{"key":"10.1016\/j.ejmech.2013.10.081_bib2","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1080\/14756360410001689540","article-title":"Carbonic anhydrases: current state of the art, therapeutic applications and future prospects","volume":"19","author":"Pastorekova","year":"2004","journal-title":"J.\u00a0Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib3","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.ejmech.2013.10.081_bib4","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1111\/j.1600-0714.2012.01147.x","article-title":"Expression of CA-IX is associated with advanced stage tumors and poor survival in oral squamous cell carcinoma patients","volume":"41","author":"P\u00e9rez-Say\u00e1ns","year":"2012","journal-title":"J.\u00a0Oral Pathol. Med."},{"key":"10.1016\/j.ejmech.2013.10.081_bib5","doi-asserted-by":"crossref","first-page":"398","DOI":"10.1053\/gast.1997.v112.pm9024293","article-title":"Carbonic anhydrase IX, MN\/CA IX: analysis of stomach complementary DNA sequence and expression in human and rat alimentary tracts","volume":"112","author":"Pastorekov\u00e1","year":"1997","journal-title":"Gastroenterology"},{"key":"10.1016\/j.ejmech.2013.10.081_bib6","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1177\/002215549804600409","article-title":"Immunohistochemistry of carbonic anhydrase isozyme IX (MN\/CA IX) in human gut reveals polarized expression in the epithelial cells with the highest proliferative capacity","volume":"46","author":"Saarnio","year":"1998","journal-title":"J.\u00a0Histochem. Cytochem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib7","first-page":"7075","article-title":"Hypoxia-inducible expression of tumor-associated carbonic anhydrases","volume":"60","author":"Wykoff","year":"2000","journal-title":"Cancer Res."},{"key":"10.1016\/j.ejmech.2013.10.081_bib8","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1016\/S0002-9440(10)64038-2","article-title":"Expression of hypoxia-inducible cell-surface transmembrane carbonic anhydrases in human cancer","volume":"158","author":"Ivanov","year":"2001","journal-title":"Am. J. Pathol."},{"key":"10.1016\/j.ejmech.2013.10.081_bib9","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.ejmech.2013.10.081_bib10","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.ejmech.2013.10.081_bib11","doi-asserted-by":"crossref","first-page":"3467","DOI":"10.1016\/j.bmcl.2010.05.009","article-title":"Carbonic anhydrase inhibitors","volume":"20","author":"Supuran","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2013.10.081_bib12","doi-asserted-by":"crossref","first-page":"2857","DOI":"10.1016\/S0960-894X(03)00581-X","article-title":"Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions","volume":"13","author":"Franchi","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2013.10.081_bib13","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/j.bmcl.2003.09.062","article-title":"Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-associated isozyme IX","volume":"14","author":"Abbate","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2013.10.081_bib14","series-title":"Carbonic Anhydrase. Its Inhibitors and Activators","first-page":"67","article-title":"Development of sulfonamide carbonic anhydrase inhibitors","author":"Supuran","year":"2004"},{"key":"10.1016\/j.ejmech.2013.10.081_bib15","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1016\/j.radonc.2009.06.019","article-title":"Imaging of CA IX with fluorescent labelled sulfonamides distinguishes hypoxic and (re)-oxygenated cells in a xenograft tumour model","volume":"92","author":"Dubois","year":"2009","journal-title":"Radiother. Oncol."},{"key":"10.1016\/j.ejmech.2013.10.081_bib16","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.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib17","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1016\/j.radonc.2011.05.045","article-title":"Specific inhibition of carbonic anhydrase IX activity enhances the in\u00a0vivo therapeutic effect of tumor irradiation","volume":"99","author":"Dubois","year":"2011","journal-title":"Radiother. Oncol."},{"key":"10.1016\/j.ejmech.2013.10.081_bib18","doi-asserted-by":"crossref","first-page":"4846","DOI":"10.1016\/j.bmcl.2006.06.064","article-title":"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","volume":"16","author":"S\u0105czewski","year":"2006","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2013.10.081_bib19","doi-asserted-by":"crossref","first-page":"3933","DOI":"10.1016\/j.bmc.2008.01.034","article-title":"Carbonic anhydrase inhibitors: inhibition of human cytosolic isozymes I and II and tumor-associated isozymes IX and XII with S-substituted 4-chloro-2-mercapto-5-methyl-benzenesulfonamides","volume":"16","author":"S\u0105czewski","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib20","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1080\/14756360600648146","article-title":"Carbonic anhydrase inhibitors. Selective inhibition of human tumor-associated isozymes IX and XII and cytosolic isozymes I and II with some substituted-2-mercapto-benzenesulfonamides","volume":"21","author":"S\u0105czewski","year":"2006","journal-title":"J.\u00a0Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib21","first-page":"1309","article-title":"Syntheses and some reactions of 3-amino-6-chloro-7-methyl-1,1-dioxo-1,4,2-benzodithiazine","volume":"75","author":"S\u0142awi\u0144ski","year":"2001","journal-title":"Pol. J. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib22","doi-asserted-by":"crossref","first-page":"1705","DOI":"10.1007\/s00706-012-0849-7","article-title":"Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro-N-(4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activity","volume":"143","author":"S\u0142awi\u0144ski","year":"2012","journal-title":"Monatsh. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib23","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1016\/0223-5234(96)85164-6","article-title":"Carbonic anhydrase inhibitors. Part 36. Inhibition of isozymes I and II with Schiff bases derived from chalkones and aromatic\/heterocyclic sulfonamides","volume":"31","author":"Supuran","year":"1996","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib24","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","article-title":"Structure validation in chemical crystallography","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Crystallogr. D Biol. Crystallogr."},{"key":"10.1016\/j.ejmech.2013.10.081_bib25","doi-asserted-by":"crossref","first-page":"2561","DOI":"10.1016\/S0021-9258(18)62326-9","article-title":"The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C","volume":"246","author":"Khalifah","year":"1971","journal-title":"J.\u00a0Biol. Med."},{"key":"10.1016\/j.ejmech.2013.10.081_bib26","series-title":"CrysAlis CCD and CrysAlis RED, Version 1.171","author":"Oxford Diffraction","year":"2005"},{"key":"10.1016\/j.ejmech.2013.10.081_bib27","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A\u00a0short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. A"},{"key":"10.1016\/j.ejmech.2013.10.081_bib28","doi-asserted-by":"crossref","first-page":"837","DOI":"10.1107\/S0021889899006020","article-title":"WinGX suite for small-molecule single-crystal crystallography","volume":"32","author":"Farrugia","year":"1999","journal-title":"J.\u00a0Appl. Cryst."},{"key":"10.1016\/j.ejmech.2013.10.081_bib29","doi-asserted-by":"crossref","first-page":"2337","DOI":"10.1021\/jm031079w","article-title":"Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX","volume":"47","author":"Casey","year":"2004","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2013.10.081_bib30","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1016\/j.bmcl.2004.12.053","article-title":"Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides\u2014a new target for the design of antitumor and antiglaucoma drugs?","volume":"15","author":"Vullo","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2013.10.081_bib31","first-page":"589","article-title":"Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay","volume":"48","author":"Alley","year":"1988","journal-title":"Cancer Res."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523413007381?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523413007381?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2022,3,11]],"date-time":"2022-03-11T23:58:34Z","timestamp":1647043114000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523413007381"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,1]]},"references-count":31,"alternative-id":["S0223523413007381"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2013.10.081","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2014,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N\u2032-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2013.10.081","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2013 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}