Synthesis and in vitro cytotoxicity evaluation of 4-aminoquinoline derivatives.
A series of 4-aminoquinoline derivatives were synthesized by the reaction of 4-chloro-7-substituted-quinolines with the corresponding mono/dialkyl amines. The structures of the synthesized compounds were confirmed by NMR and FAB-MS spectral and elemental analyses. Subsequently, the compounds were examined for their cytotoxic effects on two different human breast tumor cell lines: MCF7 and MDA-MB468. Although all compounds examined were quite effective on both cell lines, the compound N'-(7-chloro-quinolin-4-yl)-N,N-dimethyl-ethane-1,2-diamine emerged as the most active compound of the series. It was particularly potent against MDA-MB 468 cells when compared to chloroquine and amodiaquine. The compound butyl-(7-fluoro-quinolin-4-yl)-amine showed more potent effects on MCF-7 cells when compared to chloroquine. Therefore, 4-aminoquinoline can serve as the prototype molecule for further development of a new class of anticancer agents.
Zhang
Haiwen
H
Tumour Biology Group, Northeastern Ontario Regional Cancer Program at the Sudbury Regional Hospital, 41 Ramsey Lake Road, Sudbury, Ontario P3E 5J1, Canada.
Solomon
V Raja
VR
Hu
Changkun
C
Ulibarri
Gerardo
G
Lee
Hoyun
H
D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology; D000634:Aminoquinolines / Q000138:chemical synthesis / Q000494:pharmacology*; D000655:Amodiaquine / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy*; D045744:Cell Line, Tumor; D002738:Chloroquine / Q000494:pharmacology; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D011804:Quinolines / Q000138:chemical synthesis / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013329:Structure-Activity Relationship
D000588:Amines; D000634:Aminoquinolines; D000970:Antineoplastic Agents; C529177:N'-(7-chloro-quinolin-4-yl)-N,N-dimethyl-ethane-1,2-diamine; D011804:Quinolines; C529178:butyl-(7-fluoro-quinolin-4-yl)-amine; D000655:Amodiaquine; D002738:Chloroquine