Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities

dc.contributor.authorOkten, Salih
dc.contributor.authorCakmak, Osman
dc.contributor.authorErenler, Ramazan
dc.contributor.authorYuce, Onem
dc.contributor.authorTekin, Saban
dc.date.accessioned2020-06-25T18:07:36Z
dc.date.available2020-06-25T18:07:36Z
dc.date.issued2013
dc.departmentKırıkkale Üniversitesi
dc.descriptionOkten, Salih/0000-0001-9656-1803; Erenler, Ramazan/0000-0002-0505-3190
dc.description.abstractA short and easy route is described for 6,8-disubstituted derivatives of quinoline and 1,2,3,4-tetrahydroquinoline from 6,8-dibromoquinolines 2 and 7 by various substitution reactions. While copper-promoted substitution of 6,8-dibromide 2 produced monomethoxides 3 and 4, a prolonged reaction time mainly afforded dimethoxide 6 instead of 5, whose aromatization with DDQ and substitution reaction of dibromide 7 with NaOMe in the presence of CuI also gave rise to dimethoxide 6. Several 6,8-disubstituted quinolines were obtained by treatment of 6,8-dibromoquinoline (7) with n-BuLi followed by trapping with an electrophile [Si(Me)(3)Cl, S-2(Me)(2), and DMF]. Furthermore, 7 was also converted to mono and dicyano derivatives. The anticancer activities of compounds 2, 7, 6, 12, 13, 15, and 16 against HeLa, HT29, and C6 tumor cell lines were tested, and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (2) and 6,8-dimethoxyquinoline (6) showed significant anticancer activities against the tumor cell lines.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [112T394]en_US
dc.description.sponsorshipThis study was supported by grants from the Scientific and Technological Research Council of Turkey (TUBITAK, Project number: 112T394).en_US
dc.identifier.citationÖkten S., Çakmak O., Erenler R., Yüce Ö., Tekin Ş. (2013). Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities. Turkish Journal of Chemistry, 37(6), 896 - 908.en_US
dc.identifier.doi10.3906/kim-1301-30
dc.identifier.endpage908en_US
dc.identifier.issn1300-0527
dc.identifier.issue6en_US
dc.identifier.scopus2-s2.0-84887982519
dc.identifier.scopusqualityQ3
dc.identifier.startpage896en_US
dc.identifier.trdizinid161516
dc.identifier.urihttps://doi.org/10.3906/kim-1301-30
dc.identifier.urihttps://hdl.handle.net/20.500.12587/5620
dc.identifier.volume37en_US
dc.identifier.wosWOS:000326936200005
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakTR-Dizin
dc.language.isoen
dc.publisherScientific Technical Research Council Turkey-Tubitaken_US
dc.relation.ispartofTurkish Journal Of Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectAnticancer effecten_US
dc.subjectbromoquinolineen_US
dc.subjectcyanoquinolineen_US
dc.subjectlithium-bromine exchangeen_US
dc.subjectmethoxyquinolineen_US
dc.subjectquinoline derivativesen_US
dc.titleSimple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activitiesen_US
dc.typeArticle

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