Synthesis And Antiproliferative Activity Of 8-hydroxyquinoline Derivatives Containing A 1,2,3-triazole Moiety

dc.creatorDe O Freitas L.B.
dc.creatorBorgati T.F.
dc.creatorDe Freitas R.P.
dc.creatorRuiz A.L.T.G.
dc.creatorMarchetti G.M.
dc.creatorDe Carvalho J.E.
dc.creatorDa Cunha E.F.F.
dc.creatorRamalho T.C.
dc.creatorAlves R.B.
dc.date2014
dc.date2015-06-25T18:02:49Z
dc.date2015-11-26T15:05:01Z
dc.date2015-06-25T18:02:49Z
dc.date2015-11-26T15:05:01Z
dc.date.accessioned2018-03-28T22:15:49Z
dc.date.available2018-03-28T22:15:49Z
dc.identifier
dc.identifierEuropean Journal Of Medicinal Chemistry. Elsevier Masson Sas, v. 84, n. , p. 595 - 604, 2014.
dc.identifier2235234
dc.identifier10.1016/j.ejmech.2014.07.061
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84905170939&partnerID=40&md5=b06cc38df59ca3ee2de7df6c9d3573e6
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/87913
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/87913
dc.identifier2-s2.0-84905170939
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1256978
dc.descriptionTwelve novel 8-hydroxyquinoline derivatives were synthesized with good yields by performing copper-catalyzed Huisgen 1,3-dipolar cycloaddition ("click" reaction) between an 8-O-alkylated-quinoline containing a terminal alkyne and various aromatic or protected sugar azides. These compounds were evaluated in vitro for their antiproliferative activity on various cancer cell types. Protected sugar derivative 16 was the most active compound in the series, exhibiting potent antiproliferative activity and high selectivity toward ovarian cancer cells (OVCAR-03, GI50 < 0.25 μg mL -1); this derivative was more active than the reference drug doxorubicin (OVCAR-03, GI50 = 0.43 μg mL-1). In structure-activity relationship (SAR) studies, the physico-chemical parameters of the compounds were evaluated and docking calculations were performed for the α-glucosidase active site to predict the possible mechanism of action of this series of compounds. © 2014 Elsevier Masson SAS. All rights reserved.
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dc.languageen
dc.publisherElsevier Masson SAS
dc.relationEuropean Journal of Medicinal Chemistry
dc.rightsfechado
dc.sourceScopus
dc.titleSynthesis And Antiproliferative Activity Of 8-hydroxyquinoline Derivatives Containing A 1,2,3-triazole Moiety
dc.typeArtículos de revistas


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