Vol. 28, No. 8, 2017
Gomes et al.
1581
1
1
666, 1595, 1471, 1257, 1184, 1146; H NMR (500 MHz,
7.71 (d, 2H, J 8.0 Hz, 2Ar-H), 7.54 (d, 2H, J 8.0 Hz,
CDCl ) d 8.19-8.13 (m, 2H, 2Ar-H), 7.79-7.73 (m, 2H,
2Ar-H), 3.38-3.26 (m, 4H, 2CH ), 1.18 (t, 3H, J 7.1 Hz,
CH ), 1.08 (t, 3H, J 7.1 Hz, CH ); C NMR (126 MHz,
3 3
3
2
13
2
2
Ar-H), 7.48-7.37 (m, 5H, 5Ar-H), 3.37-3.24 (m, 4H,
CH ), 1.17 (t, 3H, J 7.1 Hz, CH ), 1.06 (t, 3H, J 7.1 Hz,
CDCl ) d 183.84, 179.58, 152.42, 151.23, 135.46, 134.54,
2
3
3
1
3
2
CH ); C NMR (126 MHz, CDCl ) d 184.36, 179.91,
134.17, 133.37, 132.00, 131.14 (q, J 33 Hz), 131.10,
3
3
C-F
3
1
1
4
52.67, 150.67, 136.81, 134.33, 133.94, 132.18, 131.15,
30.16, 129.56, 129.24, 128.02, 127.08, 126.60, 42.54,
2.50, 13.85, 13.29. HRMS (ESI) m/z, calcd. for C H NO
130.65, 127.15, 126.75, 124.98 (q, J 4 Hz), 124.09 (q,
JC-F 272 Hz), 42.66, 42.61, 13.84, 13.22. HRMS (ESI)
m/z, calcd. for C H F NO [M + Na] : 440.1080, found:
C-F
1
+
21
19
4
22 18
3
4
+
[M + Na] : 372.1206, found: 372.1209.
440.1079.
3
-(3,4-Dimethoxyphenyl)-1,4-dioxo-1,4-dihydronaphthalen-
-yl diethylcarbamate (7b)
3-(4-Formylphenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl
diethylcarbamate (7e)
2
After column chromatography using hexanes/EtOAc
After column chromatography using hexanes/EtOAc
(95:5) as eluent, this compound was obtained as a yellow
(
95:5) as eluent, this compound was obtained as a red solid
-1
-1
in 44% yield, mp 115-118 °C; IR (neat) n / cm 1730,
oil in 32% yield. IR (neat) n / cm 1730, 1694, 1666, 1605,
1
1
1
666, 1595, 1514, 1454, 1259, 1184, 1145, 1026; H NMR
1259, 1209, 1184, 1145; H NMR (500 MHz, CDCl )
3
(
(
500 MHz, CDCl ) d 8.20-8.12 (m, 2H, 2Ar-H), 7.81-7.73
m, 2H, 2Ar-H), 7.04 (dd, 1H, J 8.3, 2.0 Hz,Ar-H), 7.00 (d,
d 10.08 (s, 1H, CHO), 8.21-8.14 (m, 2H, 2Ar-H), 7.96 (d,
2H, J 8.2 Hz, 2Ar-H), 7.83-7.77 (m, 2H, 2Ar-H), 7.60 (d,
3
1
3
1
H, J 2.0 Hz, Ar-H), 6.95 (d, 1H, J 8.3 Hz, Ar-H), 3.94 (s,
2H, J 8.2 Hz, 2Ar-H), 3.40-3.24 (m, 4H, 2CH ), 1.18 (t,
3H, J 7.1 Hz, CH ), 1.07 (t, 3H, J 7.1 Hz, CH ); C NMR
3 3
2
1
3
H, OCH ), 3.88 (s, 3H, OCH ), 3.44-3.24 (m, 4H, 2CH ),
3
3
2
.20 (t, 3H, J 7.1 Hz, CH ), 1.12 (t, 3H, J 7.1 Hz, CH );
(126 MHz, CDCl ) d 191.98, 183.76, 179.53, 152.40,
3
3
3
1
3
C NMR (126 MHz, CDCl ) d 184.59, 179.88, 152.92,
151.16, 136.52, 135.86, 135.59, 134.56, 134.18, 131.98,
131.07, 130.98, 129.21, 127.14, 126.76, 42.67, 42.60,
13.91, 13.22. HRMS (ESI) m/z, calcd. for C H NO
3
1
1
5
50.34, 150.01, 148.48, 136.61, 134.26, 133.93, 132.27,
31.20, 127.11, 126.56, 123.67, 121.95, 113.45, 110.72,
2
2
19
5
+
5.05, 55.99, 42.58, 14.01, 13.37. HRMS (ESI) m/z, calcd.
[M + Na] : 400.1155, found: 400.1164.
+
for C H NO [M + Na] : 432.1418, found: 432.1422.
2
3
23
6
3-(3-Methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-
3
-(4-Fluorophenyl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl
2-yl diethylcarbamate (8)
diethylcarbamate (7c)
After column chromatography using hexanes/EtOAc
(95:5) as eluent, this compound was obtained as a brown
After column chromatography using hexanes/EtOAc
-
1
(95:5) as eluent, this compound was obtained as a yellow
oil in 40% yield. IR (neat) n / cm 1730, 1694, 1666,
-1
1
oil in 73% yield. IR (neat) n / cm 1730, 1666, 1593, 1504,
1593, 1454, 1360, 1337, 1259, 1186, 1145, 1051; H NMR
1
1
259, 1225, 1184, 1145; H NMR (500 MHz, CDCl )
(500 MHz, CDCl ) d 8.13-8.03 (m, 2H, 2Ar-H), 7.77-7.66
3
3
d 8.20-8.12 (m, 2H, 2Ar-H), 7.81-7.74 (m, 2H, 2Ar-H),
(m, 2H, 2Ar-H), 5.17-5.11 (m, 1H, CH), 3.48 (q, 2H,
7
3
1
.44-7.39 (m, 2H, 2Ar-H), 7.17-7.11 (m, 2H, 2Ar-H),
J 7.1 Hz, CH ), 3.41 (q, 2H, J 7.1 Hz, CH ), 3.32 (d, 2H,
J 7.3 Hz, CH ), 1.76 (s, 3H, CH ), 1.68 (s, 3H, CH ),
2 3 3
2
2
.38-3.28 (m, 4H, 2CH ), 1.19 (t, 3H, J 7.1 Hz, CH ),
2
3
1
3
.10 (t, 3H, J 7.1 Hz, CH ); C NMR (126 MHz, CDCl )
1.32 (t, 3H, J 7.1 Hz, CH ), 1.24 (t, 3H, J 7.1 Hz, CH );
3 3
3
3
1
13
d 184.25, 179.73, 163.26 (d, J 249 Hz), 152.59, 150.70,
1
1
C NMR (126 MHz, CDCl ) d 184.96, 179.67, 152.53,
3
C-F
3
35.74, 134.41, 134.04, 132.28 (d, J 8 Hz), 132.01,
151.27, 137.81, 134.50, 134.02, 133.71, 132.33, 131.19,
126.70, 126.57, 119.07, 42.61, 25.89, 23.72, 18.04, 14.17,
C-F
4
31.04, 127.09, 126.63, 125.37 (d, J 3 Hz), 115.22
C-F
2
+
(d, J 22 Hz), 42.56, 42.51, 13.92, 13.29. HRMS (ESI)
13.34. HRMS (ESI) m/z, calcd. for C H NO [M + Na] :
C-F
20 23
4
+
m/z, calcd. for C H FNO [M + Na] : 390.1112, found:
364.1519, found: 364.1520.
21
18
4
390.1116.
Antineoplastic activity
1
,4-Dioxo-3-(4-(trifluoromethyl)phenyl)-1,4-dihydro-
naphthalen-2-yl diethylcarbamate (7d)
The cell lines HL-60 and K562 were obtained from
the National Cancer Institute, Bethesda, MD, USA. All
cancer cells were maintained in RPMI 1640 (Roswell
Park Memorial Institute 1640) medium supplemented with
After column chromatography using hexanes/EtOAc
(
95:5) as eluent, this compound was obtained as a yellow
-1
oil in 48% yield. IR (neat) n / cm 1730, 1666, 1595, 1330,
1
1
-1
257, 1184, 1144, 1067, 1018; H NMR (500 MHz, CDCl )
10% fetal bovine serum, 2 mM glutamine, 100 U mL
3
-
1
d 8.21-8.14 (m, 2H, 2Ar-H), 7.82-7.76 (m, 2H, 2Ar-H),
penicillin, 100 µg mL streptomycin at 37 °C with 5%