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

Salih ÖKTEN; Osman ÇAKMAK; Ramazan ERENLER; Önem YÜCE; Şaban TEKİN

Article Details

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

Publisher:

TUBITAK

Journal:

Turkish Journal of Chemistry 2013 Vol.37 Issue 6, pp.896-908

Document Type:

Article

Publication Date:

5/2013

Document Language:

Turkish

Document ID (Org No.):

2000727284

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

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 (7) with n-BuLi followed by trapping with an  electrophile [Si(Me)3Cl, S2(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.

 

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 (7) with n-BuLi followed by trapping with an  electrophile [Si(Me)3Cl, S2(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.

Article Details

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

Publisher: TUBITAK

Journal: Turkish Journal of Chemistry 2013 Vol.37 Issue 6, pp.896-908

Document Type: Article

Publication Date: 5/2013

Document Language: Turkish

Document ID (Org No.): 2000727284

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

Issues

Authors:

Salih ÖKTEN | Osman ÇAKMAK | Ramazan ERENLER | Önem YÜCE | Şaban TEKİN

Publisher:

TUBITAK

Journal:

Turkish Journal of Chemistry 2013 Vol.37 Issue 6, pp.896-908

Document Type:

Article

Publication Date:

5/2013

Document Language:

Turkish

Document ID (Org No.):

2000727284

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527