Med Chem Res
0
C-4 ), 24.84 (C, C-17), 25.40 (C, C-16), 32.98 (C, C-15),
8.09 (C, C-14), 67.50 (C, C-11), 102.56 (C, C-8), 111.72
C, C-6), 112.77 (C, C-3), 114.74 (C, C-10), 126.02 (C,
C-5), 152.34 (C, C-9), 155.02 (C, C-4), 159.87 (C, C-2),
60.93 (C, C-7), 166.02 (C, C-12); MS [ESI]: 316.2
M ? 1].
112.28 (C, C-6), 112.45 (C, C-3), 114.42 (C, C-10), 125.84
(C, C-5), 152.39 (C, C-9), 155.05 (C, C-4), 160.68 (C,
C-2), 160.98 (C, C-7), 165.52 (C, C-12); MS [ESI]: 304.2
[M ? 1].
4
(
1
[
N-(4-methoxy-phenyl)-2-(4-methyl-2-oxo-2H-chromen-7-
yloxy)-acetamide (7j)
4
-methyl-7-(2-oxo-2-piperidin-1-yl-ethoxy) chromen-2-one
(
7g)
Yield
:
86 %; colourless crystals (MeOH); m.p:
2
10–212 °C; IR (KBr) mmax: 3354, 2912, 1708, 1668, 1539,
-
1 1
Yield : 85 %; colourless crystals (MeOH); m.p: 171–174 °C;IR
KBr) m : 2937, 2852, 2407, 1770, 1660, 1558, 1284,
1247, 1082 cm ; H NMR (CDCl /TMS, 300 MHz): 2.39
3
0
0
(
(s, 3H, H-4 ), 3.73 (s, 3H, H-17 ), 4.79 (s, 2H, H-11), 6.19
(s, 1H, H-3), 6.91–6.88 (d, 2H, H-6, 8), 7.07–7.00 (d, 2H,
H-16, 18), 7.54–7.51 (d, J = 9.0 Hz, 2H, H-15, 19), 7.72
max
-1 1
1
078 cm ; H NMR (CDCl /TMS, 300 MHz):d 1.55–1.66
3
0
(m, 6H), 2.38(s, 3H, H-4 ), 3.43–3.57 (m, 4H), 4.77 (s, 2H,
1
3
H-11), 6.13(s, 1H, H-3), 6.82(d, J = 2.5 Hz, 1H, H-8), 6.94 (d/
(d, J = 8.7 Hz, 1H, H-5), 9.88 (d, 1H, NH, H-13);
0
C
1
3
d, J = 2.5 Hz, 1H, H-6), 7.50(d, J = 8.7 Hz, 1H, H-5);
0
C
NMR (CDCl /TMS, 75 MHz): 18.56 (C, C-4 ), 55.63 (C,
3
0
NMR (CDCl /TMS, 75 MHz): 18.62 (C, C-4 ), 24.35 (C,
3
C-17 ), 67.83 (C, C-11), 102.17 (C, C-8), 111.91 (C, C-6),
C-16), 25.46 (C, C-15), 26.47 (C, C-14), 43.21 (C, C-17), 46.18
112.85 (C, C-3), 114.10 (C, C-10), 114.34 (C, C-18),
121.82 (C, C-15), 126.97 (C, C-16), 131.80 (C, C-17),
153.78 (C, C-14), 154.98 (C, C-9), 156.08 (C, C-4), 160.50
(C, C-2), 161.29 (C, C-7), 165.81 (C, C-12); MS [ESI]:
340.2 [M ? 1].
(
C, C-13), 67.20 (C, C-11), 102.01 (C, C-8), 112.26 (C, C-6),
12.35 (C, C-3), 114.20 (C, C-10), 125.73 (C, C-5), 152.45 (C,
C-9), 155.04 (C, C-4), 161.04 (C, C-2), 161.07 (C, C-7), 164.98
C, C-12); MS [ESI]: 302.2 [M ? 1].
1
(
4
-methyl-7-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethoxy]-
N-(3,4,5-trimethoxy-phenyl)-2-(4-methyl-2-oxo-2H-
chromen-2-one (7h)
chromen-7-yloxy)-acetamide (7k)
Yield: 85 %; colourless crystals (MeOH); m.p: 97–99 °C;
Yield: 88 %; colourless crystals (MeOH); m.p: 189–192 °C;
IR (KBr) m : 3074, 2981, 1712, 1651, 1483, 1257,
IR (KBr) m : 3363, 2914, 1712, 1683, 1604, 1541, 1271,
max
max
-1 1
-
080 cm ; H NMR (CDCl /TMS, 300 MHz): 2.30 (s,
1
1
1
3
3
1
1053 cm ; H NMR (CDCl /TMS,300 MHz): d 2.39 (s,
3
3
0
0
0
0
0
0
H, H-16 ), 2.39 (s, 3H, H-4 ), 2.44–2.41 (m, 4H, H-14,15),
.66–3.544 (m, 4H, H-17, 18), 4.77 (s, 2H, H-11), 6.14 (s,
H, H-3), 6.82 (s, J = 2.5 Hz, 1H, H-8), 6.94 (d/d,
3H, H-4 ), 3.61 (s, 3H, H-14 ), 3.73 (s, 6H, H-15 ,16 ), 4.82
(s, 2H, H-11), 6.23 (s, 1H, H-3), 7.01–7.07 (m, 3H, H-5, 6,
1
3
8), 7.70–7.73 (d, 2H, H-14, 18), 10.08 (s, 1H, –NH); C
0
J = 2.5 Hz, 1H, H-6), 7.53–7.50 (d, J = 8.7 Hz, 1H, H-5);
1
NMR (CDCl /TMS, 75 MHz): 18.57 (C, C-4 ), 56.21 (C,
3
3
0
0
0
C NMR (CDCl /TMS, 75 MHz): 18.70 (CH , C-4 ),
3
C-16 ), 60.57 (C, C-14 , 15,), 67.76 (C, C-11), 97.92 (C,
C-18), 102.15 (C, C-8), 111.92 (C, C-6), 112.87 (C, C-3),
114.13 (C, C-10), 127.00 (C, C-5), 134.28 (C, C-15), 134.87
(C, C-17), 153.19 (C, C-9), 153.80 (C, C-13), 154.99 (C,
C-4), 160.51 (C, C-2), 161.27 (C, C-7), 166.18 (C, C-12);
MS [ESI]: 400.2 [M ? 1].
3
4
2.00 (C, C-14), 45.00 (C, C-15), 46.01 (C, C-17), 54. 52
C, C-18), 55.01 (C, C-16’), 67.10 (C, C-11), 101.98 (C,
C-8), 112.34 (C, C-6), 112.38 (C, C-3), 114.33 (C, C-10),
25.81 (C, C-5), 152.48 (C, C-9), 155.01 (C, C-4), 160.81
C, C-2), 161.11 (C, C-7), 165.22 (C, C-12); MS [ESI]:
(
1
(
3
17.2 [M ? 1].
N-(2-hydroxy-phenyl)-2-(4-methyl-2-oxo-2H-chromen-7-
4
-methyl-7-(2-morpholin-4-yl-2-oxo-ethoxy)-chromen-2-
yloxy)-acetamide (7l)
one (7i)
Yield
:
83 %; colourless crystals (MeOH); m.p:
Yield
:
85 %; colourless crystals (MeOH); m.p:
191–193 °C; IR (KBr) mmax: 3255, 2912, 1718, 1665, 1539,
-
1
1
1
1
2
4
1
46–148 °C; IR (KBr) mmax: 3050, 2982, 1712, 1658, 1475,
257, 1075 cm ; H NMR (CDCl /TMS, 300 MHz): d
1247, 1082 cm ; H NMR (CDCl /TMS, 300 MHz): d
3
-
1
1
2.39 (s, 3H, H-4’), 4.9 (s, 2H, H-11), 6.22 (s, 1H, H-3),
6.7–6.95 (m, 2H, H-6,8), 7.03–7.07 (d, 4H, H-5, 15, 16,
17), 7.6–7.7 (m, 1H, H-18), 9.3 (s, 1H, –OH), 10.04 (s, 1H,
3
0
.38 (s, 3H, H-4 ), 3.57–3.67 (brm, 8H, H-14, 15, 17, 18),
.77 (s, 2H, H-11), 6.13(s, 1H, H-3), 6.82 (d, J = 2.5 Hz,
H, H-8), 6.94 (d/d, J = 2.5 Hz, 1H, H-6), 7.50 (d,
1
3
0
–NH). C NMR (CDCl /TMS, 75 MHz): 18.58 (C, C-4 ),
3
1
3
J = 8.7 Hz, 1H, H-5); C NMR (CDCl /TMS,75 MHz):
3
67.83 (C, C-11), 102.2 (C, C-8), 112.0 (C, C-6), 112.8 (C,
C-3), 114.2 (C, C-10), 115.7 (C, C-15), 121.8 (C, C-18),
125.1 (C, C-17), 125.9 (C, C-16), 127.0 (C, C-5), 147.9 (C,
0
1
8.62 (C, C-4 ), 42.39 (C, C-14), 45.66 (C, C-18), 66.59 (C,
C-17), 66.75 (C, C-15), 67.17 (C, C-11), 102.00 (C, C-8),
1
23