Abstract
To discover new bioactive lead compounds for medicinal purposes, 2-cyano-3-(4-substituted)-
-(quinolin-3-yl) acrylamide derivatives
, chromenes
and benzochromenes
were synthesized. The structures of the newly synthesized compounds were confirmed by elemental analyses, IR,
H NMR and
C NMR spectroscopies. In addition, the structure of compound
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)-
-(quinolin-3-yl) acrylamide (
), 3-oxo-
-(quinolin-3-yl)-3
-benzol[
] chromene-2-carboxamide (
), 2-cyano-3-(4-fluorophenyl-
-(quinolin-3-yl) acrylamide (
), 2-cyano-5-(4-(dimethyl-amino) phenyl)-
-(quinolin-3-yl) penta-2,4-dienamide (
) exhibited higher activity compared to doxorubicin (with
value of 47.9 μmol L
) as a reference drug, with
values of 29.8, 39.0, 40.0, 40.4 μmol L
, resp. Also, quinoline acrylamides containing 2,3,4-trimethoxyphenyl
, 2-chlorophenyl
, benzo[
][1,3]dioxol
, 2-methoxynaphthalen
, 2,4-dichlorophenyl
and quinoline carrying a chromene-3-carboxamide moiety
were nearly as active as doxorubicin, while quinoline acrylamides incorporating unsubstituted phenyl
,
-tolyl
, 2,4-dienamide
, 3-nitrophenyl
, 4-nitrophenyl
, 3,4-dimethoxyphenyl
and chromene
exhibited a moderate activity. In addition, quinoline with acetamide
, 4-hydroxyphenyl
, 4-dimethylaminophenyl
, 4-chlorophenyl
, 3-bromophenyl
, 4-bromophenyl
and 3-thienyl moiety
showed less activity than doxorubicin. On the other hand, quinoline having 2-methoxyphenyl
, 4-methoxyphenyl
, 4-metho xynaphthalene
and chromene-2-carboxamide
showed no activity.