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https://doi.org/10.1515/acph-2015-0030

Anti-breast cancer activity of some novel quinoline derivatives

MOSTAFA M. GHORAB ; Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
MANSOUR S. ALSAID ; Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia

Sažetak

To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-N-(quinolin-3-yl) acrylamide derivatives 2-24, chromenes 25, 26 and benzochromenes 27, 28 were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectroscopies. In addition, the structure of compound 1 was confirmed through X-ray crystallography. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. The corresponding 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-N-(quinolin-3-yl) acrylamide (15), 3-oxo-N-(quinolin-3-yl)-3H-benzol[f]chromene-2-carboxamide (27), 2-cyano-3-(4-fluorophenyl-N-(quinolin-3-yl) acrylamide (7), 2-cyano-5-(4-(dimethylamino) phenyl)-N-(quinolin-3-yl) penta-2, 4-dienamide (19) exhibited higher activity compared to doxorubicin (with IC50 value of 47.9 μmol L–1) as a reference drug, with IC50 values of 29.8, 39.0, 40.0, 40.4 μmol L–1, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl 17, 2-chlorophenyl 10, benzo[d][1,3]dioxol 12, 2-methoxynaphthalen 22, 2,4-dichlorophenyl 18 and quinoline carrying chromene-3-carboxamide moiety 25 were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl 2, p-tolyl 3, 2,4-dienamide 8, 3-nitrophenyl 13, 4-nitrophenyl 14, 3,4-dimethoxyphenyl 16 and chromene 26 exhibited moderate activity. In addition, quinolines with acetamide 1, 4-hydroxyphenyl 4, 4-dimethylaminophenyl 9, 4-chlorophenyl 11, 3-bromophenyl 20, 4-bromophenyl 21 and 3-thienyl moiety 24 showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl 5, 4-methoxyphenyl 6, 4-methoxynaphthaene 23 and chromene-2-carboxamide 28 showed no activity.

Ključne riječi

quinolineacrylamides; chromenes; benzochromenes; anti-breast cancer activity

Hrčak ID:

134873

URI

https://hrcak.srce.hr/134873

Datum izdavanja:

30.9.2015.

Posjeta: 1.137 *