I. Yildiz-Oren et al. / European Journal of Medicinal Chemistry 39 (2004) 291–298
293
Table 1
Physical, preparation, and spectral data of the synthesized compounds 5–7
Compound Y
number
Z
R
R1
R2
Mp (°C)
Yield Reaction Reaction
IR (cm–1
)
1H-NMR d ppm(J = Hz)
(recrystallization (%)
time (h) temperature
(°C)
solvent) a
5a
5b
O
O
O
O
H
H
H
H
H
49
22
1.5
140
3100, 2940, 1605–
1500, 1455–1390,
7.70–7.20 (m, 9H, C-4 H, C-5 H, C-6 H,
C-7 H and phenyl protons), 5.20 (s, 2H,
1300–1045, 950–700 CH2)
NO2
134 (B)
3
120
3120, 2950, 1630–
1595, 1533, 1458,
1345, 1230–1060,
950–695
8.58 (d, IH, C-4 H, J4,6 = 3.5 Hz),
8.20 and 8.45 (dd, 1H, C-6 H,
J6,7 = 8.8 Hz, J6,4 = 3.5 Hz), 7.60 (d, IH,
C-7 H, J7,6 = 8.8 Hz), 7.40–6.80 (m, 5H,
phenyl protons
5c
O
O
O
O
H
H
Cl
H
H
(C)
3
2
140
160
3110, 2975, 1610–
1500, 1460–1390,
1295–1050, 945–695
3110, 2890, 1630–
1585, 1525, 1458,
1348, 1270–1060,
955–700
d 7.50–7.00 (m, 8H, C-4 H, C-6 H, C-7
H and phenyl protons), 5.20 (s, 2H, CH2)
5d
NO2 138–139 (D)
42
8.50–7.50 (m, 3H, C-4 H, C-5 H, and C-7
H), 7.40–6.80 (m, 5H, phenyl protons),
5.37 (s, 2H, CH2)
5e
O
O
H
COOCH3 H
121–122 (B)
57
3
110
3100, 2995–2900,
1735, 1630–1500,
1440, 1250, 1230–
1050, 985–690
8.46–8.43 (d, 1H, C-4 H, J4,6 = 1.60 Hz),
8.19–8.06 (dd, 1H, C 6 H, J6,7 = 8.80 Hz,
J6,4 = 1.60 Hz), 7.64–7.52 (dd, 1H, C-7
H, J7,6 = 8.80 Hz), 7.40–6.90 (m, 5H,
phenyl protons), 5.34 (s, 2H, CH2), 3.95
(s, 3H, CH3)
5f
O
O
O
O
Cl H
H
H
56
74
2.5
2.5
110
110
3120, 2960–2900,
1630–1585, 1460–
1500, 1245–1042,
949–660
d 7.80–7.21 (m, 6H, C-4 H, C-5 H, C-6
H, C-7 H, C-3′ H and C-5′ H), 7.04–6.95
(dd, 2H, C-2′ H and C-6′ H and C-6′ H,
J2′,3′ and J6′,5′ = 9.2 Hz), 5.29 (s, 2H,
CH2)
8.60 (d, 1H, C-4 H, J4,6 = 2.40 Hz), 8.40–
8.20 (dd, 1H, C-6 H, J6,7 = 8.96 Hz,
J6,4 = 2.40 Hz), 7.65 (d, 1H, C-7 H,
J7,6 = 8.96 Hz), 7.35–7.23 (dd, 2H, C-3′
H and C-5′ J3′,2′ and J5′,6′ = 9.12 Hz),
7.00–6.90 (dd, 2H, C-2′ H and C-6′ H,
J2′,.3′ and J5′,6′ = 9.12 Hz), 5.34 (2H, s)
5g
Cl NO2
140–141 (D)
3110, 2960–2890,
1630–1590, 1538,
1440, 1350, 1240–
1050, 940–660
5h
O
O
Cl H
NO2 147–148 (A)
23
5
130
3148, 2950–2880,
1635–1585, 1525,
1435, 1340, 1235–
1065, 960–665
8.49–8.46 (d, 1H, C-7 H, J7,5 = 2.24 Hz),
8.40–8.20 (dd, 1H, C-5 H,
J5,4 = 8.76 Hz, J5,7 = 2.24 Hz), 7.90–7.80
(d, 1H, C-4 H, J4,5 = 8.76 Hz), 7.35–7.23
(dd, 2H, C-3′ H and C-5′, J3′,2′ and
J5′,6′ = 9.26 Hz), 7.03–6.90 (dd, 2H, c-2′
H and C-6′ H, J2′,6′ and J6′,5′ = 9.26 Hz),
5.35 (2H, s)
5i
5j
O
O
O
O
Cl Cl
NO2 88–89 (B)
39
48
3
4
120
150
3130, 2940–2900,
1600–1580, 1540,
1448, 1350, 1285–
1080, 965–660
8.10 (s, 1H, C-7 H), 7.90 (s, 1H, C-4 H),
7.34–7.23 (dd, 2H, C-3′ H and C-5′ H,
J3′,2′ and J5′,6′ = 9.26 Hz), 7.00–6.90 (dd,
2H, C-2′ H and C-6′ H, J2′,3′ and J5′,6′
9.26 Hz), 5.34 (s, 2H, CH2)
8.46–8.43 (d, 1H, C-4 H, J4,6 = 1.60 Hz),
8.19–8.07 (dd, 1H, C-6 H,
J6,7 = 8.60 Hz, J6,4 = 1.60 Hz), 7.63–7.52
(dd, 1H, C-7 H, J7,6 = 8.60 Hz) 7.33–
7.21 (dd, 2H, C-3′ H and C-5′ H, J3′,2′
and J5′,6′ = 9.26 Hz), 7.03–6.90 (dd, 2H,
C-2′ H and C-6′ H, J2′,3′, and
J6′,5′ = 9.26 Hz), 5.29 (s, 2H, CH2) 3.95
(s, 3H, CH3)
Cl COOCH3 H
145–146 (B)
3130, 2990–2880,
1743, 1630–1500,
1440, 1250, 1210–
1045, 940–660
5k
O
O
S
S
H
H
H
H
H
33
30
3
3
140
110
3100, 2995–2880,
1620–1575, 1460,
7.60–7.20 (m, 9H, C-4 H, C-5 H, C-6 H,
C-7 H and phenyl protons) 4.27 (s, 2H,
1250–1020, 950–690 CH2)
5m
NO2
53–54 (B)
3120, 2925, 1630–
1575, 1531, 1490–
1445, 1345, 1260–
1070, 970–700
8.50 (d, 1H, C-4 H, J4,6 = 2.08 Hz), 8.30–
8.20 (dd, 1H, C-6 H, J6,7 = 8.90 Hz,
J6,4 = 2.08 Hz), 7.60–7.50 (d, 1H, C-7 H,
J7,6 = 8.90 Hz), 7.46–7.22 (m, 5H, phe-
nyl protons), 4.33 (s, 2H, CH2)
5n
O
S
H
H
NO2 57–58 (D)
32
2.5
115
3140, 2940, 1630–
1579, 1535, 1425,
1345, 1275–1060,
960–695
8.30–7.80 (m, 2H, C-5 H and C-7 H), 7.60
(d, 1H, C-4 H, J4,5 = 9.10 Hz), 7.39–7.20
(m, 5H, phenyl protons), 4.33 (s, 2H,
CH2)
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