Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities
Yükleniyor...
Tarih
2013
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Scientific Technical Research Council Turkey-Tubitak
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
A 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.
Açıklama
Okten, Salih/0000-0001-9656-1803; Erenler, Ramazan/0000-0002-0505-3190
Anahtar Kelimeler
Anticancer effect, bromoquinoline, cyanoquinoline, lithium-bromine exchange, methoxyquinoline, quinoline derivatives
Kaynak
Turkish Journal Of Chemistry
WoS Q Değeri
Q3
Scopus Q Değeri
Q3
Cilt
37
Sayı
6
Künye
Ökten 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.
