K. Yamawaki et al. / Bioorg. Med. Chem. 16 (2008) 1632–1647
1641
Cl, 4.68; S, 8.47. Found: C, 41.41; H, 4.90; N, 14.55; Cl,
4.54; S, 8.46.
3.18 and 3.33 (2H, ABq, J = 17.7 Hz), 3.62 (2H, t,
J = 5.4 Hz), 4.53 (2H, t, J = 5.4 Hz), 4.65 (1H, q,
J = 6.9 Hz), 5.18 (1H, d, J = 4.8 Hz), 5.53 and 5.71
(2H, ABq, J = 14.7 Hz), 5.87 (1H, d, J = 4.8 Hz), 6.99
(1H, d, J = 3.0 Hz), 7.69 (1H, dd, J = 6.3, 8.4 Hz), 8.07
(1H, d, J = 3.0 Hz), 8.57 (1H, d, J = 8.4 Hz), 8.62 (1H,
d, J = 6.3 Hz). IR (KBr) cmꢀ1: 3400, 2938, 1777, 1629,
1540, 1497, 1467, 1450, 1368, 1323, 1288, 1240, 1189,
1159, 1134, 1095, 1035. MS (FAB): 691+(M+H)+. Anal.
Calcd for C27H27ClN8O8S2Æ4.1H2O: C, 41.51; H, 4.77;
N, 14.34; Cl, 4.54; S, 8.21. Found: C, 41.33; H, 4.56;
N, 14.36; Cl, 4.88; S, 8.39.
5.1.5. Compound 3d. Amorphous powder. 18% yield. 1H
NMR (D2O) d: 1.43 (3H, d, J = 7.2 Hz), 3.18 and 3.34
(2H, ABq, J = 18.0 Hz), 3.97 (2H, t, J = 4.8 Hz), 4.54
(2H, t, J = 4.8 Hz), 4.64 (1H, q, J = 7.2 Hz), 5.16 (1H,
d, J = 4.8 Hz), 5.53 and 5.71 (2H, ABq, J = 15.0 Hz),
5.87 (1H, d, J = 4.8 Hz), 7.00 (1H, d, J = 3.0 Hz), 7.67
(1H, dd, J = 6.3, 8.1 Hz), 8.12 (1H, d, J = 3.0 Hz), 8.59
(1H, d, J = 8.1 Hz), 8.62 (1H, d, J = 6.3 Hz). IR (KBr)
cmꢀ1: 3408, 2938, 1776, 1670, 1615, 1539, 1496, 1466,
1447, 1362, 1322, 1240, 1187, 1159, 1130, 1072, 1034.
MS (FAB): 650+(M+H)+. Anal. Calcd for
C25H24ClN7O8S2Æ4.1H2O: C, 41.48; H, 4.48; N, 13.54;
Cl, 4.90; S, 8.86. Found: C, 41.48; H, 4.40; N, 13.59;
Cl, 5.07; S, 8.88.
5.1.10. Compound 3i. Amorphous powder. 21% yield. 1H
NMR (D2O) d: 1.43 (3H, d, J = 7.5 Hz), 3.15 and 3.32
(2H, ABq, J = 17.7 Hz), 3.91(3H, s), 3.57 (2H, brs),
4.51(2H, m), 4.65 (1H, q, J = 7.5 Hz), 5.17 (1H, d,
J = 4.8 Hz), 5.55 and 5.70 (2H, ABq, J = 14.7 Hz),
5.87 (1H, d, J = 4.8 Hz), 7.00 (1H, d, J = 3.3 Hz), 7.69
(1H, dd, J = 6.0, 8.1 Hz), 8.09 (1H, d, J = 3.3 Hz), 8.59
(1H, d, J = 8.1 Hz), 8.64 (1H, d, J = 6.0 Hz). IR (KBr)
cmꢀ1: 3410, 2987, 2940, 1777, 1677, 1626, 1537, 1499,
1466, 1365, 1322, 1271, 1191, 1157, 1132, 1096, 1035.
HR-MS (FAB): Calcd for C27H28ClN8O9S2: 707.1109.
Found: 707.1106.
5.1.6. Compound 3e. Amorphous powder. 66% yield. 1H
NMR (D2O) d: 1.43 (3H, d, J = 7.2 Hz), 3.21 and 3.35
(2H, ABq, J = 18.0 Hz), 4.64 (1H, q, J = 7.2 Hz), 5.01
(2H, s), 5.17 (1H, d, J = 4.8 Hz), 5.53 and 5.74 (2H,
ABq, J = 15.0 Hz), 5.89 (1H, d, J = 4.8 Hz), 6.98(1H,
d, J = 3.3 Hz), 7.67 (1H, dd, J = 6.3, 8.1 Hz), 8.04 (1H,
d, J = 3.3 Hz), 8.44 (1H, d, J = 8.1 Hz), 8.62 (1H, d,
J = 6.3 Hz). IR (KBr) cmꢀ1: 3415, 2989, 2527, 1778,
1725, 1672, 1630, 1537, 1500, 1467, 1373, 1328, 1229,
1162, 1129, 1063, 1035. MS (ESI): 664+(M+H)+. Anal.
Calcd for C25H22ClN7O9S2Æ3.0H2O: C, 41.81; H, 3.93;
N, 13.65; Cl, 4.94; S, 8.93. Found: C, 41.75; H, 3.89;
N, 13.71; Cl, 5.08; S, 8.84.
5.1.11. Compound 3j. Amorphous powder. 24% yield. 1H
NMR (D2O) d: 1.44 (3H, d, J = 6.9 Hz), 3.18 and 3.33
(2H, ABq, J = 17.7 Hz), 3.54 (2H, t, J = 4.5 Hz), 4.49
(2H, t, J = 4.5 Hz), 4.65 (1H, q, J = 6.9 Hz), 5.17 (1H,
d, J = 5.1 Hz), 5.52 and 5.70 (2H, ABq, J = 15.0 Hz),
5.87 (1H, d, J = 5.1 Hz), 6.98 (1H, d, J = 3.3 Hz), 7.67
(1H, dd, J = 6.3, 8.1 Hz), 8.07 (1H, d, J = 3.3 Hz), 8.55
(1H, d, J = 8.1 Hz), 8.60 (1H, d, J = 6.3 Hz). IR (KBr)
cmꢀ1: 3375, 1773, 1660, 1609, 1543, 1497, 1466, 1451,
1362, 1288, 1240, 1188, 1159, 1133, 1098, 1035. MS
(FAB): 692+(M+H)+. Anal. Calcd for C26H26ClN9O8-
S2Æ4.3H2O: C, 40.58; H, 4.53; N, 16.38; Cl, 4.61; S,
8.33. Found: C, 40.46; H, 4.38; N, 16.84; Cl, 5.26; S,
7.73.
1
5.1.7. Compound 3f. Amorphous powder. 69% yield. H
NMR (D2O) d: 1.43 (3H, d, J = 6.9 Hz), 3.20 and 3.37
(2H, ABq, J = 17.7 Hz), 4.64 (1H, q, J = 6.9 Hz), 5.17
(1H, d, J = 4.8 Hz), 5.27 (2H, s), 5.56 and 5.73 (2H,
ABq, J = 15.0 Hz), 5.88 (1H, d, J = 4.8 Hz), 7.06 (1H,
d, J = 3.3 Hz), 7.70 (1H, dd, J = 6.3, 8.1 Hz), 8.07 (1H,
d, J = 3.3 Hz), 8.51 (1H, d, J = 8.1 Hz), 8.67 (1H, d,
J = 6.3 Hz). IR (KBr) cmꢀ1: 3407, 3191, 2988, 1776,
1684, 1615, 1537, 1500, 1467, 1364, 1331, 1225, 1189,
1160, 1131, 1063, 1034. MS (ESI): 663+(M+H)+. Anal.
Calcd for C25H23ClN8O8S2Æ3.9H2O: C, 40.95; H, 4.23;
N, 15.28; Cl, 4.83; S, 8.74. Found: C, 40.93; H, 4.06;
N, 15.26; Cl, 4.82; S, 8.64.
5.1.12. Compound 3k. Amorphous powder. 65% yield.
1H NMR (D2O) d: 1.43 (3H, d, J = 7.2 Hz), 3.14 and
3.31 (2H, ABq, J = 17.7 Hz), 3.53 (2H, t-like), 4.57
(2H, t-like), 4.64 (1H, q, J = 7.2 Hz), 5.17 (1H, d,
J = 4.8 Hz), 5.54 and 5.70 (2H, ABq, J = 15.0 Hz),
5.87 (1H, d, J = 4.8 Hz), 7.00 (1H, d, J = 3.3 Hz), 7.68
(1H, dd, J = 6.3, 8.4 Hz), 8.13 (1H, d, J = 3.3 Hz), 8.62
(1H, d, J = 8.4 Hz), 8.62 (1H, d, J = 6.3 Hz). IR (KBr)
cmꢀ1: 3316, 1775, 1671, 1611, 1538, 1497, 1467, 1448,
1363, 1326, 1241, 1157, 1134, 1097, 1035. MS (FAB):
728+(M+H+). Anal. Calcd for C25H26ClN9O9S3Æ3.6-
H2O: C, 37.86; H, 4.22; N, 15.90; Cl, 4.47; S, 12.13.
Found: C, 37.88; H, 4.10; N, 15.92; Cl, 4.37; S, 12.00.
5.1.8. Compound 3g. Amorphous powder. 24% yield. 1H
NMR (D2O) d: 1.44 (3H, d, J = 6.9 Hz), 3.16 and 3.31
(2H, ABq, J = 18.0 Hz), 4.43 (2H, t, J = 4.5 Hz), 4.65
(1H, q, J = 6.9 Hz), 4.68 (2H, t, J = 4.5 Hz), 5.17 (1H,
d, J = 5.1 Hz), 5.54 and 5.71 (2H, ABq, J = 15.0 Hz),
5.87 (1H, d, J = 5.1 Hz), 7.01 (1H, d, J = 3.0 Hz), 7.69
(1H, dd, J = 6.3, 8.1 Hz), 8.12 (1H, d, J = 3.0 Hz), 8.61
(1H, d, J = 8.1 Hz), 8.63 (1H, d, J = 6.3 Hz). IR (KBr)
cmꢀ1: 3415, 3193, 2987, 1777, 1718, 1673, 1614, 1537,
1497, 1466, 1447, 1364, 1328, 1225, 1188, 1135, 1080,
1034. MS (FAB): 693+(M+H)+. Anal. Calcd for
C26H25ClN8O9S2Æ3.0H2O: C, 41.80; H, 4.18; N, 15.00;
Cl, 4.75; S, 8.58. Found: C, 41.68; H, 4.19; N, 14.79;
Cl, 4.78; S, 8.91.
5.1.13. Compound 4. Amorphous powder. 68% yield. 1H
NMR (D2O + DCl) d: 1.44 (3H, d, J = 7.1 Hz), 2.80
(3H, s), 3.20 and 3.53 (2H, ABq, J = 17.9 Hz), 3.75
(2H, t, J = 5.5 Hz), 4.66 (1H, q, J = 7.1 Hz), 5.03 (2H,
t, J = 5.5 Hz), 5.23 (1H, d, J = 5.0 Hz), 5.79 (2H, s),
5.88 (1H, d, J = 5.0 Hz), 8.07 (1H,dd, J = 8.7, 5.8 Hz),
8.82 (1H, s), 8.96 (1H, d, J = 8.7 Hz), 9.05 (1H, d,
J = 5.8 Hz). IR (KBr) cmꢀ1: 3408, 1773, 1604, 1540,
5.1.9. Compound 3h. Amorphous powder. 18% yield. 1H
NMR (D2O) d: 1.43 (3H, d, J = 6.9 Hz), 1.74 (3H, s),