Synthesis a-Glucosidase Inhibition New Flavone Ethers
dissolved in 20 mL of acetone and refluxed. Progress
monitored using TLC, and upon completion, solvent was
being removed using rotary evaporator. Product was col-
lected and rinsed with diethyl ether to afford pure product.
1H), 7.70 (d, J = 8.0 Hz, 1H), 7.49–7.54 (m, 2H), 7.44 (s,
4H), 7.25 (dd, J = 8.0, 2.0 Hz, 1H), 7.10 (s, 1H), 5.20 (s,
2H), 1.29 (s, 9H); 13C-NMR (125 MHz, DMSO-d6): d
179.41, 163.24, 158.65, 156.27, 150.31, 137.26, 135.30,
134.02, 129.91, 127.62, 127.62, 126.14, 125.68, 125.47,
125.47, 125.31, 119.38, 118.39, 118.24, 115.14, 105.63,
70.74, 34.39, 31.93, 31.93, 31.93; HREI-MS: m/z calcd
for C26H24O3 [M]+ 384.1725; found 384.1729; Anal. Calcd
for C26H24O3: C, 81.22; H, 6.29; found: C, 81.23; H, 6.31.
2-(3-((4-nitrobenzyl)oxy)phenyl)-4H-chromen-4-one
(3)
Light yellow solid; yield 76%; 1H-NMR (500 MHz, DMSO-
d6): d 7.87 (t, J = 8.4 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H),
7.73 (d, J = 8.2 Hz, 2H), 7.70 (d, J = 7.2 Hz, 2H), 7.61 (d,
J = 8.2 Hz, 2H), 7.48 (t, J = 7.7 Hz, 2H), 7.39 (t,
J = 7.4 Hz, 1H), 7.30 (dd, J = 8.1, 2.3 Hz, 1H), 7.13 (s,
1H), 5.31 (s, 2H); 13C-NMR (125 MHz, DMSO-d6): d
178.28, 163.27, 158.69, 156.48, 147.98, 144.72, 135.38,
134.07, 128.96, 128.39, 128.39, 126.34, 125.47, 125.23,
123.42, 123.42, 119.53, 118.39, 118.21, 115.14, 105.97,
70.94; HREI-MS: m/z calcd for C22H15NO5 [M]+ 373.0950;
found 373.0953; Anal. Calcd for C22H15NO5: C, 70.77; H,
4.05; N, 3.75; found: C, 70.76; H, 4.05; N, 3.77.
2-(3-((2,5-bis(trifluoromethyl)benzyl)oxy)phenyl)-
4H-chromen-4-one (7)
Yellowish white solid; yield 92%; 1H-NMR (500 MHz,
DMSO-d6): d 8.24 (s, 1H), 8.07–8.10 (m, 2H), 8.02 (s, 1H),
7.86 (d, J = 7.0 Hz, 1H), 7.79–7.82 (m, 2H), 7.78 (d,
J = 8.0 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H), 7.53 (d,
J = 8.0 Hz, 1H), 7.31 (dd, J = 8.0, 2.5 Hz, 1H), 7.13 (s,
1H), 5.47 (s, 2H); 13C-NMR (125 MHz, DMSO-d6): d
178.19, 163.27, 158.86, 156.38, 140.46, 136.43, 135.72,
135.59, 133.82, 128.94, 128.37, 126.74, 126.46, 125.91,
125.37, 125.23, 123.86, 123.13, 119.68, 118.47, 118.13,
115.54, 105.63, 69.35; HREI-MS: m/z calcd for
C24H14F6O3 [M]+ 464.0847; found 464.0852; Anal. Calcd
for C24H14F6O3: C, 62.08; H, 3.04; found: C, 62.09; H,
3.02.
2-(3-(benzyloxy)phenyl)-4H-chromen-4-one (4)
White solid; yield 81%; 1H-NMR (600 MHz, DMSO-d6): d
8.30 (d, J = 8.4 Hz, 2H), 8.07 (d, J = 7.9 Hz, 1H), 7.86 (d,
J = 7.2 Hz, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.79 (d, J = 8.6
Hz, 3H), 7.75 (d, J = 7.8 Hz, 1H), 7.53 (dd, J = 14.5,
7.2 Hz, 2H), 7.30 (d, J = 7.9 Hz, 1H), 7.12 (s, 1H), 5.44
(s, 2H); 13C-NMR (125 MHz, DMSO-d6):
d
178.13,
2-(3-((3-((trifluoromethyl)thio)benzyl)oxy)phenyl)-
4H-chromen-4-one (8)
163.35, 158.62, 156.38, 137.18, 135.32, 133.98, 128.95,
128.51, 128.51, 128.37, 128.37, 128.16, 126.29, 125.63,
125.19, 119.43, 118.34, 118.53, 115.44, 105.97, 70.94;
HREI-MS: m/z calcd for C22H16O3 [M]+ 328.1099; found
328.1103; Anal. Calcd for C22H16O3: C, 80.47; H, 4.91;
found: C, 80.46; H, 4.92.
White solid; yield 76%; 1H-NMR (500 MHz, DMSO-d6): d
.07 (dd, J = 7.9, 1.3 Hz, 1H), 7.85 (dd, J = 6.9, 1.6 Hz,
1H), 7.82 (dd, J = 8.4, 0.8 Hz, 1H), 7.79 (d, J = 8.1 Hz,
2H), 7.77–7.75 (t, J = 2.0 Hz, 1H), 7.73 (d, J = 7.8 Hz, 1H),
7.68 (d, J = 8.4 Hz, 2H), 7.53 (td, J = 8.0, 4.5 Hz, 2H),
7.29 (dd, J = 7.9, 2.8 Hz, 1H), 7.10 (s, 1H), 5.35 (s, 2H);
13C-NMR (125 MHz, DMSO-d6):
d
178.12, 163.35,
2-(3-((3-(trifluoromethyl)benzyl)oxy)phenyl)-4H-
chromen-4-one (5)
158.69, 156.28, 144.39, 139.26, 135.33, 133.53, 130.47,
130.24, 128.96, 126.34, 126.23, 125.47, 125.15, 124.64,
123.36 (d, J = 261.5 Hz), 119.68, 118.57, 118.36,
115.34, 105.91, 71.43; HREI-MS: m/z calcd for
C23H15F3O3S [M]+ 428.0694; found 428.0697; Anal. Calcd
for C23H15F3O3S: C, 64.48; H, 3.53; found: C, 64.46; H,
3.51.
Light yellow solid; yield 88%; 1H-NMR (500 MHz, DMSO-
d6): d 8.05 (dd, J = 8.0, 1.5 Hz, 1H), 7.89 (s, 1H), 7.82–
7.86 (m, 3H), 7.78 (t, J = 1.5 Hz, 1H), 7.73 (t, J = 8.0 Hz,
2H), 7.69 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H),
7.52 (d, J = 6.0 Hz, 1H), 7.30 (dd, J = 8.0, 2.5 Hz, 1H),
7.10 (s, 1H), 5.37 (s, 2H); 13C-NMR (125 MHz, DMSO-d6):
d
178.28, 163.27, 158.56, 156.18, 139.35, 135.53,
133.73, 132.52, 132.28, 128.73, 128.26, 126.44, 125.63,
125.37, 125.14, 124.85 (d, J = 262.15 Hz), 124.09,
119.58, 118.35, 118.33, 115.54, 105.73, 71.33. HREI-
MS: m/z calcd for C23H15F3O3 [M]+ 396.0973; found
396.0976; Anal. Calcd for C23H15F3O3: C, 69.70; H, 3.81;
found: C, 69.72; H, 3.79.
4-((3-(4-oxo-4H-chromen-2-yl)phenoxy)methyl)
benzonitrile (9)
Light red solid; yield 83%; 1H-NMR (500 MHz, DMSO-d6):
d 8.07 (d, J = 7.8 Hz, 1H), 7.90 (d, J = 8.0 Hz, 2H), 7.86
(t, J = 7.2 Hz, 1H), 7.83 (t, J = 8.9 Hz, 1H), 7.77–7.69 (m,
4H), 7.62–7.49 (m, 2H), 7.28 (dd, J = 8.2, 2.5 Hz, 1H),
7.10 (s, 1H), 5.38 (s, 2H); 13C-NMR (125 MHz, DMSO-d6):
d
178.32, 163.24, 158.68, 156.38, 144.36, 135.37,
2-(3-((4-(tert-butyl)benzyl)oxy)phenyl)-4H-chromen-
4-one (6)
Light orange solid; yield 74%; 1H-NMR (500 MHz, DMSO-
d6): d 8.06 (d, J = 7.5 Hz, 1H), 7.83–7.86 (m, 2H), 7.73 (s,
133.91, 130.75, 130.75, 128.82, 127.41, 127.41, 126.14,
125.47, 125.38, 119.43, 119.09, 118.28, 118.39, 115.14,
112.29, 105.83, 70.74; HREI-MS: m/z calcd for
C23H15NO3 [M]+ 353.1052; found 353.1055; Anal. Calcd
Chem Biol Drug Des 2016; 87: 361–373
363