Abstract
A series of new pyrimidine analogs carrying 1,4-naphthoquinone and uracil moiety were prepared as hybrid compounds 1-(3′-chloro-1′,4′-dioxo-1′,4′-dihydronaphthalen-2′-yl)-5-substitued-1
H
-pyrimidine-2,4-diones (
6 – 9
), which might possess biological activity. The structures of new products were confirmed by IR, 1H and 13C NMR, and mass spectroscopy data. All synthesized compounds were also evaluated for their antibacterial activity. The structure – activity relationship for these compounds was studied and the results showed that 1-(3
′
-chloro-1
′
,4
′
-dioxo-1
′
,4
′
-dihydronaphthalen-2
′
-yl)-5-fluoro-1
H
-pyrimidine-2,4-dione (
9
) containing a fluorine atom exhibited
in vitro
potent antibacterial activity (MIC
50
= 1.0 μg/mL) comparable with that of the clinically useful antibacterial drug gentamicin (MIC
50
= 2.0 μg/mL) against
S. aureus and B. subtilis
. Compound
9
also exhibited the same antibacterial activity with MIC
50
= 1.0 mg/mL compared to gentamicin and ciprofloxacin against
P. aeruginosa
and with MIC
50
= 0.5 mg/mL compared to Gentamicin (MIC
50
= 0.5 mg/mL) against
E. coli
.