BULLETIN OF THE
Note
KOREAN CHEMICAL SOCIETY
DMSO-d6) δ 2.19 (s, 6H), 3.66 (s, 3H), 3.83(s, 3H), 7.12–7.26
(m, 5H), 7.42–7.47 (m, 2H), 8.09 (s, 1H), 8.47 (s, 1H); 13C
NMR (75 MHz, DMSO-d6) δ 17.35, 30.32, 56.13, 110.80,
116.51, 119.09, 120.78, 121.70, 125.21, 127.56, 128.89,
129.19, 132.07, 132.42, 133.81, 154.40, 154.97, 160.79;
LC/MS (ES+) m/z 336.1 [M + H]+.
and 1 mM EDTA (pH 7.0 phosphate buffer) in a disposable
cuvette. The mixture was vortexed and preincubated at room
temperature for 1 h. An acetate buffer solution (250 μL of 100
mM acetate, 100 mM KCl, 1 mM EDTA, pH 4.2) was added
to lower the pH of the assay solution to 4.4. The cuvettes were
incubated at 37 ꢀC for 72 h without agitation. The turbidity
of the solution at 600 nm was measured using a Thermo
Genesis 10S UV–Vis spectrometer (Thermo Fisher Scientific,
Madison, WI, USA).
3-(4-Hydroxy-3,5-dimethylstyryl)-7-methoxy-1-methyl-
1
uinolin-2(1H)-one (11d): Yield: 38%. H NMR (300 MHz,
DMSO-d6) δ 2.19 (s, 6H), 3.67 (s, 3H), 3.91 (s, 3H),
6.89–6.95 (m, 2H), 7.12–7.08 (m, 3H), 7.36 (d, J = 16.4 Hz,
1H), 7.63 (d, J = 8.6 Hz, 1H), 8.07 (s, 1H), 8.41 (s, 1H); 13C
NMR (75 MHz, DMSO-d6) δ 17.15, 30.09, 56.10, 99.04,
110.91, 114.84, 120.80, 124.95, 125.28, 127.13, 128.92,
130.47, 130.53, 132.94, 140.67, 153.91, 161.34, 161.52; LC/
MS (ES+) m/z 336.1 [M + H]+.
Acknowledgment. This study was financially supported by
the research fund of Chungnam National University in 2011.
References
3-(4-Hydroxy-3,5-dimethylstyryl)-8-methoxy-1-methyl-
quinolin-2(1H)-one (11e): Yield: 37%. 1H NMR (300 MHz,
DMSO-d6) δ 2.19 (s, 6H), 3.88 (s, 3H), 3.99 (s, 3H),
7.10–7.23 (m, 5H), 7.27–7.32 (m, 1H), 7.43 (d, J = 16.4 Hz,
1H), 8.08 (s, 1H), 8.47 (s, 1H); 13C NMR (75 MHz, DMSO-
d6) δ 17.14, 35.61, 57.27, 114.35, 120.24, 121.92, 122.93,
123.45, 124.98, 127.35, 128.45, 128.68, 129.86, 132.04,
133.13, 148.30, 154.18, 162.24; LC/MS (ES+) m/z 336.2 [M
+ H]+.
6-Hydroxy-3-(4-hydroxy-3,5-dimethylstyryl)-1-methyl-
quinolin-2(1H)-one (11f ): Yield: 42%. 1H NMR (300 MHz,
DMSO-d6) δ 2.18 (s, 6H), 3.63 (s, 3H), 7.02–7.06 (m, 2H),
7.10–7.16 (m, 3H), 7.33–7.36 (m, 1H), 7.42 (d, J = 16.4 Hz,
1H), 8.01 (s, 1H); 13C NMR (75 MHz, DMSO-d6) δ 17.15,
30.00, 112.62, 116.12, 119.48, 120.67, 121.70, 124.98,
127.31, 128.70, 128.76, 131.67, 132.17, 132.56, 152.82,
154.15, 160.51; LC/MS (ES+) m/z 322.0 [M + H]+.
7-Hydroxy-3-(4-hydroxy-3,5-dimethylstyryl)-1-methyl-
quinolin-2(1H)-one (11g): Yield: 61%. 1H NMR (300 MHz,
DMSO-d6) δ 2.18 (s, 6H), 3.59 (s, 3H), 6.73–6.80 (m, 2H),
7.06–7.12 (m, 3H), 7.33–7.39 (m, 1H), 7.53 (d, J = 8.6 Hz,
1H), 8.01 (s, 1H), 8.39 (s, 1H), 10.29 (s, 1H); 13C NMR
(75 MHz, DMSO-d6) δ 17.15, 29.87, 100.39, 112.05, 113.83,
121.01, 124.32, 124.94, 127.04, 129.03, 130.02, 130.67,
133.27, 140.89, 153.79, 160.20, 161.35; LC/MS (ES+) m/z
322.1 [M + H]+.
8-Hydroxy-3-(4-hydroxy-3,5-dimethylstyryl)-1-methyl-
quinolin-2(1H)-one (11h): Yield: 44%. 1H NMR (300 MHz,
DMSO-d6) δ 2.19 (s, 6H), 3.94 (s, 3H), 6.99–7.15 (m, 6H),
7.41 (d, J = 16.6 Hz, 1H), 8.01 (s, 1H), 8.46 (s, 1H), 10.20 (s,
1H); 13C NMR (75 MHz, DMSO-d6) δ 17.15, 35.14, 117.38,
120.32, 120.42, 123.34, 123.40, 124.96, 127.30, 128.14,
128.51, 128.74, 131.74, 133.33, 146.00, 154.12, 162.10; LC/
MS (ES+) m/z 322.0 [M + H]+.
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Bull. Korean Chem. Soc. 2015, Vol. 36, 719–722
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