Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/342388
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dc.contributor.CRUESPUNIVERSIDADE ESTADUAL DE CAMPINASpt_BR
dc.contributor.authorunicampDamião, Mariana Celestina Frojuello Costa Bernstorff-
dc.contributor.authorunicampMarçon, Henrique Magri-
dc.contributor.authorunicampPastre, Júlio Cezar-
dc.typeArtigopt_BR
dc.titleContinuous flow synthesis of the URAT1 inhibitor lesinuradpt_BR
dc.contributor.authorDamião, Mariana C. F. C. B.-
dc.contributor.authorMarçon, Henrique M.-
dc.contributor.authorPastre, Julio Cezar-
dc.subjectFarmacêuticospt_BR
dc.subjectPurificaçãopt_BR
dc.subjectQuímicapt_BR
dc.subject.otherlanguagePharmacistspt_BR
dc.subject.otherlanguagePurificationpt_BR
dc.subject.otherlanguageChemistrypt_BR
dc.description.abstractHerein, the urate anion exchange transporter 1 (URAT1) inhibitor lesinurad is synthesized from commercially available building blocks by a five-step linear continuous flow sequence. Our previously developed continuous flow platform was successfully applied to generate the 3-thio-1,2,4-triazole key intermediate 2 in 88% yield, after 55 minutes of residence time. Condensation, cyclization and S-alkylation were telescoped in a single operation without conducting solvent exchanges and intermediate purifications. Next, 1,2,4-triazole bromination and ester hydrolysis were also performed in continuous flow regime to deliver lesinurad in 68% overall yield in a total residence time of 2 hours. Our approach enables the fast generation of lesinurad and can be directly applied to produce major quantities of this important APIpt_BR
dc.relation.ispartofReaction chemistry and engineeringpt_BR
dc.publisher.cityCambridge, MApt_BR
dc.publisher.countryEstados Unidospt_BR
dc.publisherRoyal Society of Chemistrypt_BR
dc.date.issued2020-
dc.date.monthofcirculationMay.pt_BR
dc.language.isoengpt_BR
dc.description.volume5pt_BR
dc.description.issuenumber5pt_BR
dc.description.firstpage865pt_BR
dc.description.lastpage872pt_BR
dc.rightsFechadopt_BR
dc.sourceWOSpt_BR
dc.identifier.issn2058-9883pt_BR
dc.identifier.doi10.1039/c9re00483apt_BR
dc.identifier.urlhttps://pubs.rsc.org/en/content/articlelanding/2020/re/c9re00483a#!divAbstractpt_BR
dc.description.sponsorshipFUNDAÇÃO DE AMPARO À PESQUISA DO ESTADO DE SÃO PAULO - FAPESPpt_BR
dc.description.sponsordocumentnumber2014/26378-2; 2015/18572-6; 2018/25233-1; 2013/07607-8pt_BR
dc.date.available2020-06-01T19:25:03Z-
dc.date.accessioned2020-06-01T19:25:03Z-
dc.description.provenanceSubmitted by Susilene Barbosa da Silva (susilene@unicamp.br) on 2020-06-01T19:25:03Z No. of bitstreams: 0. Added 1 bitstream(s) on 2020-06-03T12:23:47Z : No. of bitstreams: 1 000532366700013.pdf: 3227068 bytes, checksum: 0d4e8862815257ab4624a4727ff4533d (MD5)en
dc.description.provenanceMade available in DSpace on 2020-06-01T19:25:03Z (GMT). No. of bitstreams: 0 Previous issue date: 2020en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/342388-
dc.contributor.departmentSem informaçãopt_BR
dc.contributor.departmentSem informaçãopt_BR
dc.contributor.departmentDepartamento de Química Orgânicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.contributor.unidadeInstituto de Químicapt_BR
dc.subject.keywordToolpt_BR
dc.identifier.source000532366700013pt_BR
dc.creator.orcidSem informaçãopt_BR
dc.creator.orcid0000-0001-8481-8413pt_BR
dc.creator.orcid0000-0001-9972-425Xpt_BR
dc.type.formArtigopt_BR
dc.description.sponsorNoteThe authors gratefully acknowledge financial support from the São Paulo Research Foundation – FAPESP (J. C. P., awards no. 2014/26378-2 and 2014/25770-6); M. D., award no. 2015/18572-6; H. M., award no. 2018/25233-1). We are also thankful to the Obesity and Comorbidities Research Center – OCRC (FAPESP Award No. 2013/07607-8) for providing us with the UNIQSIS flow system used in this work. Dr. Marjorie Bruder (National Laboratory of Biosciences, LNBio – Brazil) is acknowledged for HRMS analysespt_BR
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