Med Chem Res
1
3
(
(
(
(
(
C-4΄), 137.39 (C-4), 134.16 (C-5΄), 125.55 (C-6), 123.26
C-3), 124.17 (C-7), 123.10 (C-14), 116.32 (C-6΄), 115.43
C-5), 111.14 (C-4a΄), 109.71 (C-10), 107.20 (C-3΄), 104.36
C-4a), 102.11 (C-8΄), 58.41 (OCH ), 57.23 (OCH ΄), 22.70
Hz, H-8), 3.83 (3H, s, OCH ΄), 2.72 (3H, s, CH ); C NMR
3
3
(125 MHz, DMSO-d ): δ 169.24 (C-11), 159.61 (C-2),
6
C
159.15 (C-2΄), 156.50 (C-8a), 152.95 (C-8a΄), 148.38 (C-9),
146.10 (C-6΄), 144.60 (C-4), 140.95 (C-4΄), 138.60 (C-7),
132.04 (C-5΄), 120.05 (C-7΄), 127.20 (C-3), 125.14 (C-3΄),
121.27 (C-4a΄), 120.42 (C-8), 119.91 (C-14), 119.74 (C-4a),
117.42 (C-5), 116.31 (C-8΄), 111.97 (C-6), 111.62 (C-10),
56.52 (OCH ΄), 16.49 (CH ); MS: (+ESI) (m/z): 460.10 (M
3
3
+
CH ); MS (+ESI) (m/z): 490.11 (M+H) ; Anal. Calcd. for
3
C H O N S (489.50): C, 61.34; H, 3.91; N, 8.58. Found:
2
5 19 6 3
C, 61.30; H, 3.87; N, 8.62%.
E)-8-Methoxy-3(2-(2-(1-(8-methoxy-2-oxo-2H-chro-
men-3-yl)ethylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-
-one (7f). Yellow solid; Yield: 68.0%; m.p. 255–257 °C;
(
3
3
+
+H) ; Anal. Calcd. for C H O N S (459.47): C, 62.74;
2
4 17 5 3
2
H, 3.73; N, 9.15. Found: C, 62.70; H, 3.77; N, 9.19%.
(E)-7-Methoxy-3-(1-(2-(4-(2-oxo-2H-chromen-3-yl)thia-
zol-2-yl)hydrazono)ethyl)-2H-chrom-en-2-one (7i). Yellow
solid; Yield: 69.6%; m.p. 262–264 °C; IR (KBr, cm
max: 3437.75 (N–H), 1725.27 (O–C=O), 1565.01 (C=N);
−1
IR (KBr, cm ) vmax: 3422.83 (N–H), 1733.31 (O–C=O),
1
1
625.03 (C=N); H NMR (500 MHz, DMSO-d ): δ 11.45
6
H
−
1
(
(
1H, s, N–H), 8.56 (1H, s, H-4), 8.17 (1H, s, H-4΄), 7.80
1H, s, H-10), 7.40 (1H, dd, J = 6.5, 2.5 Hz, H-5΄),
)
v
1
7
.35–7.31 (5H, m, H-5, H-6, H-6΄, H-7, H-7΄), 3.97 (3H, s,
H NMR (500 MHz, DMSO-d ): δH 11.43 (1H, s, N-H),
6
1
3
OCH ), 3.86 (3H, s, OCH ΄), 2.30 (3H, s, CH ); C NMR
8.14 (1H, s, H-4), 8.83 (1H, s, H-4΄), 7.78 (1H, s, H-5΄),
7.79 (1H, s, H-10), 7.62 (1H, t, J = 8.5 Hz, H-7), 7.47-55
(3H, m, H-6, H-6΄, H-8΄), 7.39 (2H, d, J = 6.5 Hz, H-5, H-
8), 3.93 (3H, s, OCH ΄), 2.35 (3H, s, CH ); C NMR (125
MHz, DMSO-d ): δ 168.22 (C-11), 159.61 (C-2), 159.15
(C-2΄), 156.22 (C-8a), 151.05 (C-8a΄), 146.23 (C-9), 146.10
(C-6΄), 144.31 (C-4), 139.39 (C-4΄), 137.48 (C-7), 134.06
(C-5΄), 124.48 (C-7΄), 127.23 (C-3), 124.14 (C-3΄), 120.07
(C-4a΄), 121.40 (C-8), 117.91 (C-14), 117.04 (C-4a), 116.23
(C-5), 116.31 (C-8΄), 113.76 (C-6), 111.43 (C-10), 51.11
3
3
3
(
125 MHz, DMSO-d ): δC 170.13 (C-11), 165.25 (C-2),
6
1
8
5
1
(
(
63.21 (C-2΄), 157.20 (C-8a΄), 146.70 (C-7΄), 144.62 (C-
a), 142.32 (C-9), 142.21 (C-4΄), 138.38 (C-4), 134.15 (C-
΄), 122.22 (C-6), 121.26 (C-3), 121.19 (C-7), 121.10 (C-
4), 118.92 (C-6΄), 113.01 (C-5), 100.10 (C-4a΄), 106.62
1
3
3
3
6
C
C-10), 107.43 (C-3΄), 103.30 (C-4a), 101.01 (C-8΄), 56.32
OCH ), 55.32 (OCH ΄), 24.33 (CH ); MS: (+ESI) (m/z):
3
3
3
+
4
90.10 (M+H) ; Anal. Calcd. for C H O N S (489.50):
25 19 6 3
C, 61.34; H, 3.91; N, 8.58. Found: C, 61.32; H, 3.95; N,
.61%.
E)-8methoxy-3-(2-(2-(1-(6-nitro-2oxo-2H-chromen-3-
yl)ethylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one
+
8
(OCH ΄), 18.81 (CH ); MS: (+ESI) (m/z): 460.09 (M+H) ;
Anal. Calcd. for C H O N S (459.47): C, 62.74; H, 3.73;
3
3
(
24 17 5 3
N, 9.15. Found: C, 62.78; H, 3.78; N, 9.20%.
(
(
1
7g). Yellow solid; Yield: 61.9%; m.p. 267–269 °C; IR
(E)-8-Methoxy-3-(1-(2-(4-(2-oxo-2H-chromen-3-yl)thia-
−
1
KBr, cm ) v : 3245.34 (N–H), 1723.63 (O–C=O),
zol-2-yl)hydrazono)ethyl)-2H-chrom-en-2-one (7j). Yellow
max
1
−1
618.09 (C=N); H NMR (500 MHz, DMSO-d ): δ 10.25
solid; Yield: 70.4%; m.p. 258–260 °C; IR (KBr, cm )
6
H
(
5
7
1H, s, N-H), 8.48 (1H, s, H-4), 8.39 (1H, d, J = 2.5 Hz H-
΄), 7.98 (1H, s, H-4΄), 7.67 (1H, dd, J = 9.0, 2.5 Hz, H-7΄),
.45 (1H, s, H-10), 7.34–7.39 (2H, m, H-5, H-7), 7.28–7.32
vmax: 3438.52 (N–H), 1723.93 (O–C=O), 1605.61 (C=N);
1
H NMR (500 MHz, DMSO-d ): δH 11.45 (1H, s, N-H),
6
8.58 (1H, s, H-4), 8.15 (1H, s, H-4΄), 7.82 (1H, d, J =
7.5Hz, H-5΄), 7.79 (1H, s, H-10), 7.63 (1H, t, J = 8.5 Hz, H-
7), 7.46 (1H, d, J = 8.0 Hz, H-7΄), 7.40 (2H, t, J = 7.0 Hz,
H-6, H-6΄), 7.32 (2H, t, J = 6.5 Hz, H-5, H-8), 3.95 (3H, s,
(
2H, m, H-6, H-8΄), 3.01 (3H, s, OCH ), 2.11 (3H, s, CH );
3
3
1
3
C NMR (125 MHz, DMSO-d ): δ 169.32 (C-11), 158.32
6
C
(
(
(
(
(
(
C-2΄), 158.35 (C-2), 153.29 (C-8a΄), 147.82 (C-7΄), 142.27
C-8a), 141.21 (C-9), 141.11 (C-4΄), 136.36 (C-5΄), 133.45
C-4), 123.87 (C-6), 123.11 (C-3), 121.34 (C-14), 120.24
C-7), 112.09 (C-6΄), 113.56 (C-5), 111.11 (C-4a΄),110.76
C-10), 106.32 (C-4a), 104.21 (C-3΄), 103.79 (C-8΄), 55.11
1
3
OCH ΄), 2.35 (3H, s, CH ); C NMR (125 MHz, DMSO-
3
3
d ): δ 170.20 (C-11), 157.41 (C-2), 158.10 (C-2΄), 157.56
6
C
(C-8a), 152.01 (C-8a΄), 147.81 (C-9), 146.22 (C-6΄), 144.63
(C-4), 143.25 (C-4΄), 137.22 (C-7), 134.13 (C-5΄), 122.45
(C-7΄), 128.11 (C-3), 126.13 (C-3΄), 123.20 (C-4a΄), 122.22
(C-8), 120.02 (C-14), 120.74 (C-4a), 120.32 (C-5), 119.21
+
OCH ), 18.90 (CH ); MS (+ESI) (m/z): 505.10 (M+H) ;
3
3
Anal. Calcd. for C H O N S (504.47): C, 57.14; H, 3.20;
2
4 16 7 4
N, 11.11. Found: C, 57.19; H, 3.25; N, 11.15%.
E)-6-Methoxy-3-(1-(2-(4-(2-oxo-2H-chromen-3-yl)thia-
zol-2-yl)hydrazono)ethyl)-2H-chrom-en-2-one (7h). Yellow
(C-8΄), 114.02 (C-6), 112.32 (C-10), 58.11 (OCH ΄), 20.21
3
+
(
(CH ); MS: (+ESI) (m/z): 460.08 (M+H) ; Anal. Calcd.
3
for C H O N S (459.47): C, 62.74; H, 3.73; N, 9.15.
2
4 17 5 3
−
1
solid; Yield: 69.6%; m.p. 270–272 °C; IR (KBr, cm
)
Found: C, 62.78; H, 3.78; N, 9.20%.
v
max: 3437.57 (N–H), 1724.77 (O–C=O), 1576.92 (C=N);
(E)-6-Nitro-3-(1-(2-(4-(2-oxo-2H-chromen-3-yl)thiazol-
2-yl)hydrazono)ethyl)-2H-chromen-2-one (7k). Yellow
1
H NMR (500 MHz, DMSO-d ): δH 11.43 (1H, s, N-H),
8
6
−
1
.55 (1H, s, H-4), 8.13 (1H, s, H-4΄), 7.80 (1H, s, H-5΄),
solid; Yield: 70.6%; m.p. 271–273 °C; IR (KBr, cm
)
7
.77 (1H, s, H-10), 7.62 (1H, t, J = 6.0 Hz, H-7), 7.43 (1H,
v
max: 3432.43 (N–H), 1722.54 (O–C=O), 1617.26 (C=N);
1
d, J = 8.0 Hz, H-8΄), 7.39 (2H, dd, J = 6.5, 2.0 Hz, H-5, H-
΄), 7.36 (1H, t, J = 8.5 Hz, H-6), 7.20 (1H, dd, J = 8.5, 2.5
H NMR (500 MHz, DMSO-d ): δH 11.40 (1H, s, N-H),
8.45 (1H, s, H-4), 8.11 (1H, s, H-4΄), 7.98 (1H, s, H-5΄),
6
7