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

Authors : Salih ÖKTEN, Osman ÇAKMAK, Ramazan ERENLER, Önem YÜCE, Şaban TEKİN

Pages : 896-908

Doi:10.3906/kim-1301-30

View : 17 | Download : 10

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :A short and easy route is described for 6,8-disubstituted derivatives of quinoline and 1,2,3,4-tetrahydroquinoli- ne 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 insert ignore into journalissuearticles values(7); with n-BuLi followed by trapping with an electrophile [Siinsert ignore into journalissuearticles values(Me);3Cl, S2insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values(2); and 6,8-dimethoxyquinoline insert ignore into journalissuearticles values(6); showed significant anticancer activities against the tumor cell lines.
Keywords : Anticancer effect, bromoquinoline, cyanoquinoline, lithium bromine exchange, methoxyquinoline, quinoline derivatives