{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T09:11:09Z","timestamp":1790845869942,"version":"4.1.0"},"reference-count":85,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2019,11,1]],"date-time":"2019-11-01T00:00:00Z","timestamp":1572566400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2019,11,1]],"date-time":"2019-11-01T00:00:00Z","timestamp":1572566400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"DOI":"10.13039\/501100004410","name":"The Scientific and Technological Research Council of Turkey","doi-asserted-by":"publisher","award":["2214-A\/1059B141601251"],"award-info":[{"award-number":["2214-A\/1059B141601251"]}],"id":[{"id":"10.13039\/501100004410","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008770","name":"Anadolu University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008770","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2019,11]]},"DOI":"10.1016\/j.bioorg.2019.103222","type":"journal-article","created":{"date-parts":[[2019,8,28]],"date-time":"2019-08-28T02:04:05Z","timestamp":1566957845000},"page":"103222","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":45,"special_numbering":"C","title":["Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors"],"prefix":"10.1016","volume":"92","author":[{"given":"Cem","family":"Yamali","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Halise Inci","family":"Gul","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdulilah","family":"Ece","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silvia","family":"Bua","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Angeli","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroshi","family":"Sakagami","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ertan","family":"Sahin","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.bioorg.2019.103222_b0005","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.bioorg.2019.103222_b0010","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":"10.1016\/j.bioorg.2019.103222_b0015","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.bioorg.2019.103222_b0020","doi-asserted-by":"crossref","first-page":"290","DOI":"10.1016\/j.bioorg.2018.03.027","article-title":"Anticancer effects of new dibenzenesulfonamides by inducing apoptosis and autophagy pathways and their carbonic anhydrase inhibitory effects on hCA I, hCA II, hCA IX, hCA XII isoenzymes","volume":"78","author":"Gul","year":"2018","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0025","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1016\/j.bioorg.2018.01.021","article-title":"New anticancer drug candidates sulfonamides as selective hCA IX or hCA XII inhibitors","volume":"77","author":"Gul","year":"2018","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0030","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1517\/13543776.2013.798648","article-title":"Anticancer carbonic anhydrase inhibitors: a patent review (2008\u20132013)","volume":"23","author":"Monti","year":"2013","journal-title":"Expert Opin. Ther. Pat."},{"key":"10.1016\/j.bioorg.2019.103222_b0035","doi-asserted-by":"crossref","first-page":"48","DOI":"10.3390\/metabo7030048","article-title":"Carbonic anhydrase inhibition and the management of hypoxic tumors","volume":"7","author":"Supuran","year":"2017","journal-title":"Metabolites"},{"key":"10.1016\/j.bioorg.2019.103222_b0040","doi-asserted-by":"crossref","first-page":"42857","DOI":"10.18632\/oncotarget.17143","article-title":"Inhibition of pH regulation as a therapeutic strategy in hypoxic human breast cancer cells","volume":"8","author":"Meehan","year":"2017","journal-title":"Oncotarget"},{"key":"10.1016\/j.bioorg.2019.103222_b0045","doi-asserted-by":"crossref","first-page":"1149","DOI":"10.4155\/fmc.14.68","article-title":"Sulfonamides and their isosters as carbonic anhydrase inhibitors","volume":"6","author":"Carta","year":"2014","journal-title":"Future Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0050","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.bioorg.2019.103222_b0055","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.bioorg.2019.103222_b0060","doi-asserted-by":"crossref","first-page":"84","DOI":"10.18632\/oncotarget.422","article-title":"Recent developments in targeting carbonic anhydrase IX for cancer therapeutics","volume":"3","author":"McDonald","year":"2012","journal-title":"Oncotarget"},{"key":"10.1016\/j.bioorg.2019.103222_b0065","doi-asserted-by":"crossref","first-page":"9517","DOI":"10.1007\/s13277-015-3692-8","article-title":"Carbonic anhydrase IX overexpression regulates the migration and progression in oral squamous cell carcinoma","volume":"36","author":"Yang","year":"2015","journal-title":"Tumour Biol."},{"key":"10.1016\/j.bioorg.2019.103222_b0070","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1517\/14740338.2014.897328","article-title":"Safety of carbonic anhydrase inhibitors","volume":"13","author":"Swenson","year":"2014","journal-title":"Expert Opin. Drug Saf."},{"key":"10.1016\/j.bioorg.2019.103222_b0075","doi-asserted-by":"crossref","first-page":"98","DOI":"10.5306\/wjco.v3.i7.98","article-title":"Inhibition of carbonic anhydrase IX as a novel anticancer mechanism","volume":"3","author":"Supuran","year":"2012","journal-title":"World J. Clin. Oncol."},{"key":"10.1016\/j.bioorg.2019.103222_b0080","doi-asserted-by":"crossref","first-page":"3230","DOI":"10.1021\/jm800121c","article-title":"Carbonic anhydrase inhibitors: bioreductive nitro-containing sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII","volume":"51","author":"D'Ambrosio","year":"2008","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0085","doi-asserted-by":"crossref","first-page":"36","DOI":"10.3390\/metabo8020036","article-title":"Amino acids as building blocks for carbonic anhydrase inhibitors","volume":"8","author":"Chiaramonte","year":"2018","journal-title":"Metabolites"},{"key":"10.1016\/j.bioorg.2019.103222_b0090","first-page":"1","article-title":"Selective inhibition of carbonic anhydrase IX over carbonic anhydrase XII in breast cancer cells using benzene sulfonamides: disconnect between activity and growth inhibition","volume":"13","author":"Mam","year":"2018","journal-title":"PLoS ONE"},{"key":"10.1016\/j.bioorg.2019.103222_b0095","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. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0100","doi-asserted-by":"crossref","first-page":"5311","DOI":"10.1016\/j.bmc.2015.07.066","article-title":"Exploring new Probenecid-based carbonic anhydrase inhibitors: synthesis, biological evaluation and docking studies","volume":"23","author":"Mollica","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0105","doi-asserted-by":"crossref","first-page":"2569","DOI":"10.1016\/j.bmc.2017.03.027","article-title":"Synthesis and carbonic anhydrase inhibition of a series of SLC-0111 analogs","volume":"25","author":"Carta","year":"2017","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0110","doi-asserted-by":"crossref","first-page":"963","DOI":"10.1080\/13543784.2018.1548608","article-title":"Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors","volume":"27","author":"Supuran","year":"2018","journal-title":"Expert Opin. Investig. Drugs."},{"key":"10.1016\/j.bioorg.2019.103222_b0115","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.bioorg.2018.11.014","article-title":"SLC-0111 enaminone analogs, 3\/4-(3-aryl-3-oxopropenyl) aminobenzenesulfonamides, as novel selective subnanomolar inhibitors of the tumor-associated carbonic anhydrase isoform IX","volume":"83","author":"Eldehna","year":"2019","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0120","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1517\/13543784.12.2.283","article-title":"Indisulam: an anticancer sulfonamide in clinical development","volume":"12","author":"Supuran","year":"2003","journal-title":"Expert Opin. Investig. Drugs"},{"key":"10.1016\/j.bioorg.2019.103222_b0125","doi-asserted-by":"crossref","first-page":"1816","DOI":"10.1158\/1078-0432.CCR-06-0249","article-title":"A randomized phase II pharmacokinetic and pharmacodynamic study of indisulam as second-line therapy in patients with advanced non-small cell lung cancer","volume":"13","author":"Talbot","year":"2007","journal-title":"Clin. Cancer Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0130","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1016\/j.ejmech.2014.02.023","article-title":"4-Functionalized 1,3-diarylpyrazoles bearing benzenesulfonamide moiety as selective potent inhibitors of the tumor associated carbonic anhydrase isoforms IX and XII","volume":"76","author":"Khloya","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0135","first-page":"217","article-title":"Targeted treatment for advanced soft tissue sarcoma: profile of pazopanib","volume":"6","author":"Rajendra","year":"2013","journal-title":"Onco. Targets Ther."},{"key":"10.1016\/j.bioorg.2019.103222_b0140","doi-asserted-by":"crossref","first-page":"2527","DOI":"10.1158\/1535-7163.MCT-14-0255","article-title":"Pazopanib, a novel multitargeted kinase inhibitor, shows potent in vitro antitumor activity in gastric cancer cell lines with FGFR2 amplification","volume":"13","author":"Kim","year":"2014","journal-title":"Mol. Cancer Ther."},{"key":"10.1016\/j.bioorg.2019.103222_b0145","doi-asserted-by":"crossref","first-page":"2267","DOI":"10.2217\/fon.15.112","article-title":"Feasibility, efficacy and safety of tyrosine kinase inhibitor treatment in hemodialyzed patients with renal cell cancer: 10 years of experience","volume":"11","author":"Czarnecka","year":"2015","journal-title":"Future Oncol."},{"key":"10.1016\/j.bioorg.2019.103222_b0150","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1007\/s11912-007-0007-2","article-title":"Pazopanib: a novel multitargeted tyrosine kinase inhibitor","volume":"9","author":"Sonpavde","year":"2007","journal-title":"Curr. Oncol. Rep."},{"key":"10.1016\/j.bioorg.2019.103222_b0155","doi-asserted-by":"crossref","first-page":"8177","DOI":"10.1039\/c2cc33415a","article-title":"Polypharmacology of sulfonamides: pazopanib, a multitargeted receptor tyrosine kinase inhibitor in clinical use, potently inhibits several mammalian carbonic anhydrases","volume":"48","author":"Winum","year":"2012","journal-title":"Chem. Commun. (Camb.)"},{"key":"10.1016\/j.bioorg.2019.103222_b0160","doi-asserted-by":"crossref","first-page":"786","DOI":"10.1016\/j.ejmech.2014.11.059","article-title":"Recent advances in bioactive pyrazoles","volume":"97","author":"Kucukguzel","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0165","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1016\/j.ejmech.2014.12.023","article-title":"Recent advanced in bioactive systems containing pyrazole fused with a five membered heterocycle","volume":"97","author":"Raffa","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0170","doi-asserted-by":"crossref","first-page":"1497","DOI":"10.1016\/S0149-2918(00)80005-3","article-title":"Celecoxib, a selective cyclooxygenase-2 inhibitor for the treatment of rheumatoid arthritis and osteoarthritis","volume":"21","author":"Goldenberg","year":"1999","journal-title":"Clin. Ther."},{"key":"10.1016\/j.bioorg.2019.103222_b0175","doi-asserted-by":"crossref","first-page":"2457","DOI":"10.2165\/11208240-000000000-00000","article-title":"Celecoxib: a review of its use for symptomatic relief in the treatment of osteoarthritis, rheumatoid arthritis and ankylosing spondylitis","volume":"71","author":"McCormack","year":"2011","journal-title":"Drugs"},{"key":"10.1016\/j.bioorg.2019.103222_b0180","doi-asserted-by":"crossref","first-page":"11397","DOI":"10.1074\/jbc.275.15.11397","article-title":"The cyclooxygenase-2 inhibitor celecoxib induces apoptosis by blocking Akt activation in human prostate cancer cells independently of Bcl-2","volume":"275","author":"Hsu","year":"2000","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0185","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1177\/107327480200902S04","article-title":"Celecoxib: a specific COX-2 inhibitor with anticancer properties","volume":"9","author":"Koki","year":"2002","journal-title":"Cancer Control."},{"key":"10.1016\/j.bioorg.2019.103222_b0190","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1586\/era.13.47","article-title":"Targeted therapy for non-small-cell lung cancer: past, present and future","volume":"13","author":"Forde","year":"2013","journal-title":"Expert Rev. Anticancer Ther."},{"key":"10.1016\/j.bioorg.2019.103222_b0195","doi-asserted-by":"crossref","first-page":"360","DOI":"10.1186\/s12967-018-1729-7","article-title":"The ruxolitinib effect: understanding how molecular pathogenesis and epigenetic dysregulation impact therapeutic efficacy in myeloproliferative neoplasms","volume":"16","author":"Greenfield","year":"2018","journal-title":"J. Transl. Med."},{"key":"10.1016\/j.bioorg.2019.103222_b0200","doi-asserted-by":"crossref","first-page":"1451","DOI":"10.1016\/j.bmc.2012.10.029","article-title":"New selective carbonic anhydrase IX inhibitors: synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides","volume":"21","author":"Rogez-Florent","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0205","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1021\/ml100232q","article-title":"[I]-Celecoxib analogues as SPECT tracers of cyclooxygenase-2 in inflammation","volume":"2","author":"Uddin","year":"2011","journal-title":"ACS Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2019.103222_b0210","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. Biol. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0215","first-page":"5341","article-title":"Quantitative structure-cytotoxicity relationship of oleoylamides","volume":"35","author":"Sakagami","year":"2015","journal-title":"Anticancer Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0220","doi-asserted-by":"crossref","first-page":"1619","DOI":"10.3109\/14756366.2016.1160077","article-title":"Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides","volume":"31","author":"Gul","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0225","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1080\/14756366.2016.1209495","article-title":"Synthesis and bioactivity studies of 1-aryl-3-(2-hydroxyethylthio)-1-propanones","volume":"31","author":"Unluer","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0230","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1080\/14756366.2016.1221825","article-title":"Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases","volume":"31","author":"Yamali","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0235","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1080\/14756366.2016.1243536","article-title":"Designing, synthesis and bioactivities of 4-[3-(4-hydroxyphenyl)-5-aryl-4,5-dihydro-pyrazol-1-yl]benzenesulfonamides","volume":"32","author":"Gul","year":"2017","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0240","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1080\/14756366.2016.1254207","article-title":"Microwave-assisted synthesis and bioevaluation of new sulfonamides","volume":"32","author":"Gul","year":"2017","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0245","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.21873\/anticanres.11421","article-title":"Quantitative structure-cytotoxicity relationship of chalcones","volume":"37","author":"Sakagami","year":"2017","journal-title":"Anticancer Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0250","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.21873\/anticanres.11412","article-title":"Induction of apoptosis in human oral keratinocyte by doxorubicin","volume":"37","author":"Sakagami","year":"2017","journal-title":"Anticancer Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0255","doi-asserted-by":"crossref","first-page":"1770","DOI":"10.2174\/1871520618666180525085445","article-title":"Synthesis and cytotoxicities of new azafluorenones with apoptotic mechanism of action and cell cycle analysis","volume":"18","author":"Gul","year":"2018","journal-title":"Anticancer Agents Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0260","doi-asserted-by":"crossref","first-page":"2366","DOI":"10.1007\/s00044-018-2242-5","article-title":"Cytotoxicity, apoptosis, and QSAR studies of phenothiazine derived methoxylated chalcones as anticancer drug candidates","volume":"27","author":"Yamali","year":"2018","journal-title":"Med. Chem. Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0265","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1016\/j.bioorg.2018.12.028","article-title":"Synthesis and bioactivities of pyrazoline benzensulfonamides as carbonic anhydrase and acetylcholinesterase inhibitors with low cytotoxicity","volume":"84","author":"Ozmen Ozgun","year":"2019","journal-title":"Bioorg. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0270","doi-asserted-by":"crossref","DOI":"10.1371\/journal.pone.0053415","article-title":"Survival of patients with oral cavity cancer in Germany","volume":"8","author":"Listl","year":"2013","journal-title":"PLoS ONE"},{"key":"10.1016\/j.bioorg.2019.103222_b0275","first-page":"5434","article-title":"Impact of tumoral carbonic anhydrase IX and Ki-67 expression on survival in oral squamous cell carcinoma patients","volume":"14","author":"Brockton","year":"2017","journal-title":"Oncol. Lett."},{"key":"10.1016\/j.bioorg.2019.103222_b0280","doi-asserted-by":"crossref","first-page":"375","DOI":"10.3390\/ijms20020375","article-title":"Investigation of the prognostic role of carbonic anhydrase 9 (CAIX) of the cellular mRNA\/Protein level or soluble CAIX protein in patients with oral squamous cell carcinoma","volume":"20","author":"Eckert","year":"2019","journal-title":"Int. J. Mol. Sci."},{"key":"10.1016\/j.bioorg.2019.103222_b0285","doi-asserted-by":"crossref","first-page":"417","DOI":"10.1016\/j.oraloncology.2011.11.015","article-title":"Tumor-associated carbonic anhydrase XII is linked to the growth of primary oral squamous cell carcinoma and its poor prognosis","volume":"48","author":"Chien","year":"2012","journal-title":"Oral Oncol."},{"key":"10.1016\/j.bioorg.2019.103222_b0290","first-page":"5262","article-title":"Carbonic anhydrase IX, an endogenous hypoxia marker, expression in head and neck squamous cell carcinoma and its relationship to hypoxia, necrosis, and microvessel density","volume":"61","author":"Beasley","year":"2001","journal-title":"Cancer Res."},{"key":"10.1016\/j.bioorg.2019.103222_b0295","doi-asserted-by":"crossref","first-page":"1077","DOI":"10.1242\/jcs.072207","article-title":"Carbonic anhydrase IX (CA9) modulates tumor-associated cell migration and invasion","volume":"124","author":"Shin","year":"2011","journal-title":"J. Cell Sci."},{"key":"10.1016\/j.bioorg.2019.103222_b0300","doi-asserted-by":"crossref","first-page":"226","DOI":"10.4161\/cam.23257","article-title":"Carbonic anhydrase IX: a hypoxia-controlled \u201ccatalyst\u201d of cell migration","volume":"7","author":"Svastova","year":"2013","journal-title":"Cell. Adh. Migr."},{"key":"10.1016\/j.bioorg.2019.103222_b0305","doi-asserted-by":"crossref","first-page":"1089","DOI":"10.1002\/jps.21293","article-title":"Current topics in computer-aided drug design","volume":"97","author":"Taft","year":"2008","journal-title":"J. Pharm. Sci."},{"key":"10.1016\/j.bioorg.2019.103222_b0310","first-page":"1","article-title":"Towards more effective acetylcholinesterase inhibitors: a comprehensive modelling study based on human acetylcholinesterase protein\u2013drug complex","volume":"11","author":"Ece","year":"2019","journal-title":"J. Biomol. Struct. Dyn."},{"key":"10.1016\/j.bioorg.2019.103222_b0315","doi-asserted-by":"crossref","first-page":"5646","DOI":"10.1016\/j.bmcl.2013.08.019","article-title":"Effect of incorporating a thiophene tail in the scaffold of acetazolamide on the inhibition of human carbonic anhydrase isoforms I, II, IX and XII","volume":"23","author":"Biswas","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2019.103222_b0320","first-page":"241","article-title":"e-Pharmacophore mapping combined with virtual screening and molecular docking to identify potent and selective inhibitors of P90 ribosomal S6 kinase (RSK)","volume":"13","author":"Ece","year":"2016","journal-title":"Turk. J. Pharm. Sci."},{"key":"10.1016\/j.bioorg.2019.103222_b0325","doi-asserted-by":"crossref","first-page":"1347","DOI":"10.1021\/jm960803q","article-title":"Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib)","volume":"40","author":"Penning","year":"1997","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0330","doi-asserted-by":"crossref","first-page":"4744","DOI":"10.1021\/jm8001422","article-title":"Novel quinolinonyl diketo acid derivatives as HIV-1 integrase inhibitors: design, synthesis, and biological activities","volume":"51","author":"Di Santo","year":"2008","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0335","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1016\/j.ejmech.2009.12.042","article-title":"Synthesis and antimicrobial activities of novel 1,5-diaryl pyrazoles","volume":"45","author":"Ragavan","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0340","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1016\/j.ejmech.2015.09.021","article-title":"Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII","volume":"103","author":"Ibrahim","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0345","doi-asserted-by":"crossref","first-page":"406","DOI":"10.1016\/j.bmcl.2015.11.105","article-title":"Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors","volume":"26","author":"Abdellatif","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.bioorg.2019.103222_b0350","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1002\/jhet.3118","article-title":"Anti-inflammatory exploration of sulfonamide containing diaryl pyrazoles with promising COX-2 selectivity and enhanced gastric safety profile","volume":"55","author":"Laxmikant","year":"2018","journal-title":"J. Het. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0355","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr A"},{"key":"10.1016\/j.bioorg.2019.103222_b0360","unstructured":"Small-Molecule Drug Discovery Suite 2019-2, Schr\u00f6dinger, LLC, New York, NY, 2019."},{"key":"10.1016\/j.bioorg.2019.103222_b0365","unstructured":"Schr\u00f6dinger Release 2019-2: Schr\u00f6dinger Suite 2019-2 Protein Preparation Wizard; Epik, Schr\u00f6dinger, LLC, New York, NY, 2016; Impact, Schr\u00f6dinger, LLC, New York, NY, 2016; Prime, Schr\u00f6dinger, LLC, New York, NY, 2019."},{"key":"10.1016\/j.bioorg.2019.103222_b0370","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1007\/s10822-013-9644-8","article-title":"Protein and ligand preparation: parameters, protocols, and influence on virtual screening enrichments","volume":"27","author":"Sastry","year":"2013","journal-title":"J. Comput. Aided Mol. Des."},{"key":"10.1016\/j.bioorg.2019.103222_b0375","unstructured":"Schr\u00f6dinger Release 2019-2: LigPrep, Schr\u00f6dinger, LLC, New York, NY, 2019."},{"key":"10.1016\/j.bioorg.2019.103222_b0380","unstructured":"Schr\u00f6dinger Release 2019-2: Glide, Schr\u00f6dinger, LLC, New York, NY, 2019."},{"key":"10.1016\/j.bioorg.2019.103222_b0385","doi-asserted-by":"crossref","first-page":"6177","DOI":"10.1021\/jm051256o","article-title":"Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes","volume":"49","author":"Friesner","year":"2006","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0390","doi-asserted-by":"crossref","first-page":"1540","DOI":"10.3109\/14756366.2016.1156675","article-title":"Inhibitory effects of benzimidazole containing new phenolic Mannich bases on human carbonic anhydrase isoforms hCA I and II","volume":"31","author":"Gul","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0395","doi-asserted-by":"crossref","first-page":"1678","DOI":"10.3109\/14756366.2015.1126715","article-title":"The inhibitory effects of phenolic Mannich bases on carbonic anhydrase I and II isoenzymes","volume":"31","author":"Yamali","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0400","first-page":"843","article-title":"Hormetic and anti-radiation effects of tropolone-related compounds","volume":"24","author":"Kantoh","year":"2010","journal-title":"In Vivo"},{"key":"10.1016\/j.bioorg.2019.103222_b0405","doi-asserted-by":"crossref","first-page":"1426","DOI":"10.2174\/1871520617666170327123909","article-title":"Synthesis and cytotoxic activities of difluoro-dimethoxy chalcones","volume":"17","author":"Yamali","year":"2017","journal-title":"Anticancer Agents Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0410","doi-asserted-by":"crossref","first-page":"818","DOI":"10.3109\/14756366.2015.1070263","article-title":"Synthesis of mono Mannich bases of 2-(4-hydroxybenzylidene)-2,3-dihydroinden-1-one and evaluation of their cytotoxicities","volume":"31","author":"Tugrak","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0415","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1080\/14756366.2016.1217852","article-title":"Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines","volume":"31","author":"Kucukoglu","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0420","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.3109\/14756366.2016.1140755","article-title":"Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol","volume":"31","author":"Inci Gul","year":"2016","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"10.1016\/j.bioorg.2019.103222_b0425","first-page":"4117","article-title":"Search of new cytotoxic crude materials against human oral squamous cell carcinoma using 1H NMR-based metabolomics","volume":"34","author":"Suzuki","year":"2014","journal-title":"Anticancer Res."}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206819306935?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206819306935?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,23]],"date-time":"2025-09-23T07:55:57Z","timestamp":1758614157000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206819306935"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11]]},"references-count":85,"alternative-id":["S0045206819306935"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2019.103222","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2019,11]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis, biological evaluation and in silico modelling studies of 1,3,5-trisubstituted pyrazoles carrying benzenesulfonamide as potential anticancer agents and selective cancer-associated hCA IX isoenzyme inhibitors","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2019.103222","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2019 Elsevier Inc. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"103222"}}