Original scientific paper

https://doi.org/10.2478/acph-2014-0030

Design, synthesis and potential anti-proliferative activity of some novel 4-aminoquinoline derivatives

MOSTAFA M. GHORAB ; Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia
MANSOUR S. AL-SAID ; Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Kingdom of Saudi Arabia
REEM K. ARAFA ; Pharmaceutical Chemistry Department, Faculty of Pharmacy, Cairo University, Cairo, Egypt

Abstract

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

Hrčak ID:

121074

URI

https://hrcak.srce.hr/121074

Publication date:

30.9.2014.

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