H. Yoshizawa et al. / Bioorg. Med. Chem. 12 (2004) 4221–4231
4229
ꢁ
1
t, J ¼ 7:2 Hz), 3.05 and 3.49 (2H, ABq, J ¼ 18:0 Hz),
8.61 (1H,m); IR (KBr) cm 1773, 1649, 1556, 1523,
1460, 1385; Anal Calcd for C22 Æ1.1HClÆ4H O:
4
.11 (2H, q, J ¼ 7:2 Hz), 5.04 (1H, d, J ¼ 4:2 Hz), 5.13
H
27
N
9
O
5
S
2
2
and 5.61 (2H, ABq, J ¼ 13:8 Hz), 5.69 (1H, d,
C, 39.22; H, 5.4; Cl, 5.79; N, 18.71; S, 9.52. Found: C,
39.16; H, 5.34; Cl, 5.90; N, 18.85; S, 9.43.
J ¼ 4:2 Hz), 8.05–8.2 (2H, m), 8.45–8.6 (1H, m), 9.25–
ꢁ
1
9
1
C
.4 (2H, m); IR (KBr) cm 1775, 1666, 1617, 1526,
485,
1455,
Æ2.6H
1.96. Found: C, 42.3; H, 4.58; N, 18.55; S, 11.94.
1390;
Anal
Calcd
for
19
H
19
N
7
O
5
S
2
2
O: C, 42.55; H, 4.55; N, 18.28; S,
4.31. Compound 2e
1
2e was obtained as an amorphous powder in 48% yield
from 2e ; H NMR (D
0
1
2
O) d 1.34 (3H, t, J ¼ 7:2 Hz), 3.3
4
2
.27. Compound 2a
and 3.75 (2H, ABq, J ¼ 18 Hz), 3.34 (2H, t, J ¼ 6:3 Hz),
3
.82 (2H, t, J ¼ 6:3 Hz), 4.39 (2H, q, J ¼ 7:2 Hz), 5.34
a was obtained as an amorphous powder in 19% yield
0
(1H, d, J ¼ 5:1 Hz), 5.48 and 5.73 (2H, ABq,
1
6 2
from 2a ; H NMR (DMSO-d +D O) d 1.21 (3H, t,
J ¼ 15 Hz), 5.93 (1H, d, J ¼ 5:1 Hz), 8.43 (2H, d,
ꢁ
1
J ¼ 7:5 Hz), 3.2–3.25 (4H, m), 3.05 and 3.55 (2H, ABq,
J ¼ 18 Hz), 4.12 (2H, q, J ¼ 7:5 Hz), 5.1 (1H, d,
J ¼ 4:8 Hz), 5.12 and 5.62 (2H, ABq, J ¼ 13:5 Hz), 5.73
J ¼ 6:6 Hz), 9.19 (2H, d, J ¼ 6:6 Hz); IR (KBr) cm
1775, 1668, 1616, 1527, 1456, 1393; Anal Calcd for
Æ1.3HClÆ4.5H O: C, 37.53; H, 5.05; Cl,
6.55; N, 17.90; S, 9.11. Found: C, 37.48; H, 4.98; Cl,
C
22
H
25
N
9
O
6
S
2
2
(
1H, d, J ¼ 4:8 Hz), 8.10 (2H, d, J ¼ 6:6 Hz), 9.31 (2H,
ꢁ
1
d, J ¼ 6:6 Hz); IR (KBr) cm 1773, 1616, 1521, 1466,
6.63; N, 18.17; S, 8.95.
1
3
3
395; Anal Calcd for C21
9.13; H, 5.16; Cl, 6.05; N, 17.38; S, 9.95. Found: C,
H
24
N
8
O
5
S
2
2
Æ1.1HClÆ4H O: C,
9.18; H, 5.17; Cl, 6.13; N, 17.26; S, 9.95.
4.32. Compound 2f
2f was obtained as an amorphous powder in 16% yield
from 2f ; H NMR (D
0
1
4
2
.28. Compound 2b
2
O) d 1.34 (3H, t, J ¼ 6:9 Hz), 1.70
(
3H, d, J ¼ 7:5 Hz), 3.30 and 3.70 (1H, ABq,
b was obtained as an amorphous powder in 12% yield
0
J ¼ 17:7 Hz), 4.36 (2H, q, J ¼ 6:9 Hz), 4.4 (1H, m), 5.26
and 5.50 (2H, ABq, J ¼ 14:4 Hz), 5.33 (1H, d,
J ¼ 4:8 Hz), 5.93 (1H, d, J ¼ 4:8 Hz), 8.18 (2H, d,
1
from 2b ; H NMR (DMSO-d
6 2
+D O) d 1.21 (3H, t,
J ¼ 6:9 Hz), 3.05 and 3.52 (2H, ABq, J ¼ 18 Hz), 3.32
ꢁ
1
(
2H, m), 4.16 (2H, q, J ¼ 6:9 Hz), 4.57 (2H, m), 5.0 and
J ¼ 7:2 Hz), 8.79 (2H, d, J ¼ 7:2 Hz); IR (KBr) cm
5
5
9
1
.45 (2H, ABq, J ¼ 14:1 Hz), 5.08 (1H, d, J ¼ 5:1 Hz),
1777, 1727, 1669, 1608, 1517, 1465, 1397; Anal Calcd for
C H N O S Æ1.6HClÆ4.2H O: C, 37.24; H, 4.95; Cl,
.73 (1H, d, J ¼ 5:1 Hz), 7.66 (2H, d, J ¼ 7:5 Hz),
22
25
9
6
2
2
ꢁ
1
.15 (2H, d, J ¼ 7:5 Hz); IR (KBr) cm 1773, 1642,
7.99; N, 17.76; S, 9.04. Found: C, 37.03; H, 5.02; Cl,
7.91; N, 17.85; S, 8.92.
519,
1484,
1456,
1398;
Anal
Calcd
for
C H N O S Æ1.1HClÆ5.2H O: C, 36.96; H, 5.24; Cl,
21
24
8
6
2
2
5.71; N, 16.42; S, 9.4. Found: C, 36.69; H, 5.18; Cl, 5.63;
N, 16.40; S, 9.36.
4.33. Compound 2g
2g was obtained as an amorphous powder in 53% yield
from 2g ; H NMR (D
0
1
4
2
.29. Compound 2c
2
O) d 1.34 (3H, t, J ¼ 6:9 Hz),
3
.06 (2H, t, J ¼ 6:6 Hz), 3.26 and 3.70 (2H, ABq,
c was obtained as an amorphous powder in 25% yield
0
J ¼ 18 Hz), 3.42 (2H, t, J ¼ 6:6 Hz), 4.37 (2H, q,
J ¼ 6:9 Hz), 5.24 and 5.43 (2H, ABq, J ¼ 14:7 Hz), 5.31
(1H, d, J ¼ 4:5 Hz), 5.91 (1H, d, J ¼ 4:5 Hz), 8.12 (2H,
1
from 2c ; H NMR (DMSO-d
6 2
+D O) d 1.21 (3H, t,
J ¼ 6:9 Hz), 2.99 and 3.50 (2H, ABq, J ¼ 18 Hz), 3.04
ꢁ
1
(
2H, m), 3.61 (2H, m), 4.15 (2H, q, J ¼ 6:9 Hz), 4.70 and
d, J ¼ 7:5 Hz), 8.74 (2H, d, J ¼ 7:5 Hz); IR (KBr) cm
5
5
8
1
.22 (2H, ABq, J ¼ 13:2 Hz), 5.07 (1H, d, J ¼ 5:1 Hz),
1774, 1718, 1604, 1517, 1461, 1396; Anal Calcd for
Æ1.2HClÆ4H O: C, 38.22; H, 4.99; Cl, 6.15;
N, 18.23; S, 9.27. Found: C, 38.55; H, 4.91; Cl, 6.27; N,
.73 (1H, d, J ¼ 5:1 Hz), 6.91 (1H, m), 7.11 (1H, m),
C
22
H
25
N
9
O
6
S
2
2
ꢁ
1
.43 (1H, m), 8.65 (1H, m); IR (KBr) cm 1767, 1649,
1455,
556,
1520,
1389;
Anal
Calcd
for
O: C, 37.41; H, 5.38; Cl, 5.26;
18.47; S, 9.35.
C
N, 18.7; S, 9.51. Found: C, 37.61; H, 5.14; Cl, 5.39; N,
21
H
25
N
9
O
5
S
2
Æ1HClÆ5H
2
1
8.98; S, 9.37.
4.34. Compound 2h
2
h was obtained as an amorphous powder in 14% yield
1
0
4
2
.30. Compound 2d
from 2h ; H NMR (DMS0-d ) d 1.22 (3H, t,
6
J ¼ 7:2 Hz), 3.14 (2H, m), 3.37 and 3.52 (2H, ABq,
J ¼ 17:7 Hz), 4.18 (2H, q, J ¼ 7:2 Hz), 4.43 (2H, m),
5.19 (1H, d, J ¼ 5:1 Hz), 5.30 and 5.41 (2H, ABq,
J ¼ 14 Hz), 5.9 (1H, m), 8.03 (2H, d, J ¼ 6:9 Hz), 8.16
(1H, m), 8.36 (2H, br s), 8.76 (2H, d, J ¼ 6:9 Hz), 9.56
d was obtained as an amorphous powder in 22% yield
0
1
from 2d ; H NMR (DMSO-d +D O) d 1.22 (3H, t,
6
2
J ¼ 7:2 Hz), 1.86 (2H, m), 2.89 (2H, t, J ¼ 7:5 Hz), 2.96
and 3.47 (2H, ABq, J ¼ 18 Hz), 3.36 (2H, t, J ¼ 7:5 Hz),
ꢁ
1
4
.15 (2H, q, J ¼ 7:2 Hz), 4.67 and 5.16 (2H, ABq,
(1H, d, J ¼ 8:1 Hz); IR (KBr) cm 1783, 1752, 1676,
J ¼ 14:1 Hz), 5.04 (1H, d, J ¼ 5:1 Hz), 5.69 (1H, d,
1637, 1593, 1532, 1464, 1383; HR-FABMS calcd for
O
þ
J ¼ 5:1 Hz), 6.88 (1H, m), 6.96 (1H, m), 8.42 (1H, m),
C
22
H
26
N
9
7
S
2
[(M+H) ]: 592.1397, found: 592.1395.