{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T18:26:42Z","timestamp":1760898402169},"reference-count":26,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2017,3,1]],"date-time":"2017-03-01T00:00:00Z","timestamp":1488326400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"funder":[{"DOI":"10.13039\/501100004281","name":"National Science Centre","doi-asserted-by":"publisher","award":["2015\/19\/N\/NZ7\/00938"],"award-info":[{"award-number":["2015\/19\/N\/NZ7\/00938"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2017,3]]},"DOI":"10.1016\/j.ejmech.2017.01.028","type":"journal-article","created":{"date-parts":[[2017,1,22]],"date-time":"2017-01-22T14:16:15Z","timestamp":1485094575000},"page":"79-87","update-policy":"http:\/\/dx.doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":23,"special_numbering":"C","title":["Synthesis and biological evaluation of fluorinated N -benzoyl and N -phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7- O -sulfamate as steroid sulfatase inhibitors"],"prefix":"10.1016","volume":"128","author":[{"given":"Mateusz","family":"Da\u015bko","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maja","family":"Przyby\u0142owska","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Janusz","family":"Rachon","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maciej","family":"Mas\u0142yk","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Konrad","family":"Kubi\u0144ski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Majus","family":"Misiak","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andrzej","family":"Sk\u0142adanowski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sebastian","family":"Demkowicz","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2017.01.028_bib1","doi-asserted-by":"crossref","first-page":"1399","DOI":"10.1038\/sj.bjc.6602130","article-title":"Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats","volume":"91","author":"Ireson","year":"2004","journal-title":"Br. J. Cancer"},{"key":"10.1016\/j.ejmech.2017.01.028_bib2","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/0303-7207(91)90116-A","article-title":"Intracrinology","volume":"78","author":"Labrie","year":"1991","journal-title":"Mol. Cell. Endocrinol."},{"key":"10.1016\/j.ejmech.2017.01.028_bib3","doi-asserted-by":"crossref","first-page":"44350","DOI":"10.1039\/C4RA07135B","article-title":"Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: synthesis and biological activity","volume":"4","author":"Kozak","year":"2014","journal-title":"RSC Adv."},{"key":"10.1016\/j.ejmech.2017.01.028_bib4","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1002\/ddr.21245","article-title":"Phosphate and thiophosphate biphenyl analogs as steroid sulfatase inhibitors","volume":"76","author":"Demkowicz","year":"2015","journal-title":"Drug Dev. Res."},{"key":"10.1016\/j.ejmech.2017.01.028_bib5","doi-asserted-by":"crossref","first-page":"358","DOI":"10.1016\/j.ejmech.2015.06.051","article-title":"Synthesis of bicoumarin thiophosphate derivatives as steroid sulfatase inhibitors","volume":"101","author":"Demkowicz","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib6","doi-asserted-by":"crossref","first-page":"32594","DOI":"10.1039\/C5RA01614B","article-title":"Synthesis and steroid sulfatase inhibitory activities of N-alkanoyl tyramine phosphates and thiophosphates","volume":"5","author":"Demkowicz","year":"2015","journal-title":"RSC Adv."},{"key":"10.1016\/j.ejmech.2017.01.028_bib7","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1080\/10286020.2015.1054815","article-title":"Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors","volume":"17","author":"Kozak","year":"2015","journal-title":"J.\u00a0Asian Nat. Prod. Res."},{"key":"10.1016\/j.ejmech.2017.01.028_bib8","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1002\/ddr.21281","article-title":"Steroid sulfatase inhibitors based on phosphate and thiophosphate flavone analogs","volume":"76","author":"Kozak","year":"2015","journal-title":"Drug Dev. Res."},{"key":"10.1016\/j.ejmech.2017.01.028_bib9","doi-asserted-by":"crossref","first-page":"11508","DOI":"10.1021\/bi00036a025","article-title":"Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone-3-O-sulfamate","volume":"34","author":"Purohit","year":"1995","journal-title":"Biochemistry"},{"key":"10.1016\/j.ejmech.2017.01.028_bib10","doi-asserted-by":"crossref","first-page":"7634","DOI":"10.1021\/acs.jmedchem.5b00386","article-title":"Discovery and development of the aryl O-sulfamate pharmacophore for oncology and women's health","volume":"19","author":"Thomas","year":"2015","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib11","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1210\/er.2004-0003","article-title":"Steroid sulfatase: molecular biology, regulation, and inhibition","volume":"26","author":"Reed","year":"2005","journal-title":"Endocr. Rev."},{"key":"10.1016\/j.ejmech.2017.01.028_bib12","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1111\/j.1749-6632.1996.tb16226.x","article-title":"Regulation and inhibition of steroid sulfatase activity in breast cancer","volume":"784","author":"Purohit","year":"1996","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"10.1016\/j.ejmech.2017.01.028_bib13","doi-asserted-by":"crossref","first-page":"1068","DOI":"10.1021\/jm970527v","article-title":"Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase","volume":"41","author":"Woo","year":"1998","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib14","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1016\/j.jfluchem.2006.05.006","article-title":"Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products","volume":"127","author":"B\u00e9gu\u00e9","year":"2006","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib15","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1016\/j.jfluchem.2006.01.011","article-title":"Fluorine in medicinal chemistry: a review of anti-cancer agents","volume":"127","author":"Isanbor","year":"2006","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib16","doi-asserted-by":"crossref","first-page":"1013","DOI":"10.1016\/j.jfluchem.2006.06.007","article-title":"Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules","volume":"127","author":"Kirk","year":"2006","journal-title":"J.\u00a0Fluor. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib17","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1111\/cbdd.12652","article-title":"Synthesis and biological evaluation of fluorinated 3-phenylcoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors","volume":"87","author":"Demkowicz","year":"2016","journal-title":"Chem. Biol. Drug Des."},{"key":"10.1016\/j.ejmech.2017.01.028_bib18","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.molcata.2006.03.051","article-title":"A\u00a0solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst","volume":"255","author":"Maheswara","year":"2006","journal-title":"J.\u00a0Mol. Catal. A Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib19","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1039\/JS8682100053","article-title":"VI. - On the artificial production of coumarin and formation of its homologues","volume":"21","author":"Perkin","year":"1868","journal-title":"J.\u00a0Chem. Soc."},{"key":"10.1016\/j.ejmech.2017.01.028_bib20","doi-asserted-by":"crossref","first-page":"1477","DOI":"10.1080\/00397910903097310","article-title":"Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as reusable catalyst and solvent for the Knoevenagel condensation reaction","volume":"40","author":"Valizadeh","year":"2010","journal-title":"Synth. Commun."},{"key":"10.1016\/j.ejmech.2017.01.028_bib21","doi-asserted-by":"crossref","first-page":"4682","DOI":"10.1021\/jo050070u","article-title":"Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by Tellurium-Triggered cyclizations","volume":"70","author":"Dittmer","year":"2005","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib22","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1016\/j.tetlet.2008.10.133","article-title":"A\u00a0novel synthesis of coumarins employing triphenyl(\u03b1-carboxymethylene)phosphorane imidazolide as a C-2 synthon","volume":"50","author":"Upadhyay","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2017.01.028_bib23","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1159\/000469248","article-title":"Purification and properties of arylsulfatase C from human placenta","volume":"37","author":"Vaccaro","year":"1987","journal-title":"Enzyme"},{"key":"10.1016\/j.ejmech.2017.01.028_bib24","doi-asserted-by":"crossref","first-page":"2155","DOI":"10.1021\/jm901705h","article-title":"Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template","volume":"53","author":"Woo","year":"2010","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib25","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J.\u00a0Comput. Chem."},{"key":"10.1016\/j.ejmech.2017.01.028_bib26","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1016\/S0960-0760(01)00119-4","article-title":"Purification, characterization and crystallization of human placental estrone\/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum","volume":"78","author":"Hernandez-Guzman","year":"2001","journal-title":"J.\u00a0Steroid Biochem. Mol. Biol."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523417300387?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523417300387?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2024,6,21]],"date-time":"2024-06-21T23:56:31Z","timestamp":1719014191000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523417300387"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,3]]},"references-count":26,"alternative-id":["S0223523417300387"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2017.01.028","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2017,3]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2017.01.028","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2017 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}