Abstract
A series of (
E
) 4
H
-pyrano[3,2-
h
]quinoline-3-carbonitrile (
5a
–
f
) and (
E
) ethyl 4
H
-pyrano[3,2-
h
]quinoline-3-carboxylate (
6a
–
f
) derivatives were synthesized by interaction of (
E
) 2-(4-chloro/bromo/fluorostyryl)-8-hydroxyquinoline (
3a
–
c
) with
α
-cyano-
p
-chloro/bromocinnamonitriles (
4a
,
b
) and ethyl
α
-cyano-
p
-chloro/bromocinnamates (
4c
,
d
), respectively. Structures of these compounds were established on the basis of IR,
1
H NMR,
13
C NMR,
13
C NMR–DEPT,
13
C NMR–APT, and MS data. The new compounds were evaluated for antitumor activities against three different human tumor cell lines MCF-7, HCT, and HepG-2. The results of antitumor evaluation revealed that compounds
5a
,
d
and
6a
,
c
,
d
inhibited the growth of cancer cells compared to Vinblastine. The structure–activity relationships were discussed.
Graphical abstract