Acta Pharm. 64 (2014) 285-297
Original research paper
Design,
synthesis and potential anti-proliferative activity of some novel
4-aminoquinoline derivatives
MOSTAFA M. GHORAB, MANSOUR S. AL-SAID and REEM K. ARAFA
1 Department of Pharmacognosy, College of Pharmacy,
King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of
Saudi Arabia
2 Pharmaceutical Chemistry Department, Faculty of
Pharmacy, Cairo University, Cairo, Egypt
Accepted May 20, 2014
Novel nineteen compounds based on a 4-aminoquinoline scaffold were designed and synthesized as potential anti-proliferative agents. The new compounds were N-substituted at the 4-position by aryl or heteroaryl 1-9, quinolin-3-yl 10, 2-methylquinolin-3-yl 11, thiazol-2-yl 12, and dapsone moieties 13, 14 and 18. Bis-compounds 15, 16 and 19 were also synthesized to assess their biological activity. All the newly synthesized comounds were tested for in vitro antiproliferative activity against the MCF-7 breast cancer cell line. Seventeen of the novel compounds showed higher activity than the reference drug doxorubicin. The corresponding 7-(trifluoromethyl)-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine 1, N-(7-(trifluoromethyl)quinolin-4-yl)quinolin-3-amine (10), 2-methyl-N-(7-trifluorome-thyl)quinolin-4-yl)quinolin-3-amine (11) and N-(4-(4-aminophenylsulf-onyl)phenyl)-7-chloroquinolin-4-amine (13) were almost twice to thrice as potent as doxorubicin.
Keywords: 4-aminoquinolines,
bis-compounds, dapsone, antiproliferative activity