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3.12 (2H, t –CH2–CH2–), 3.79 (3H, s, OCH3), 4.68 (2H, s,
–CH2–C6H5), 7.00–7.34 (7H, m, H-30, H-50, H-2000, H-3000,
H-4000, H-5000, H-6000), 7.82–7.94 (6H, m, H-200, H-300, H-500,
H-600, H-20, H-60), 8.90 (1H, s, NH–CH2–C6H5). FAB-MS
(m/z): 510 (M??2), 509 (M??1). 13C NMR: d 22.81
(–CH2 of pyridazinone), d 28.71 (–CH2 of pyridazinone), d
48.33 (–NH–CH2), d 55.85 (–OCH3), d 153.75 (C=N of
pyridazinone), d 166.35 (C=O), d 179.20 (C=S). DEPT: d
22.11 (–CH2 of pyridazinone), d 27.67 (–CH2 of pyridaz-
inone), d 47.70 (–CH2NH), d 55.32 (–OCH3). Anal. Calcd.
for C25H24N4O4S2: C = 59.04, H = 4.76, N = 11.02,
S = 12.61. Found: C = 58.98, H = 4.72, N = 11.01,
S = 12.58.
DEPT (DMSO, d): d 15.92 (–CH2CH3), d 22.75 (–CH2 of
pyridazinone), d 28.13 (–CH2CH3), d 28.49 (–CH2 of py-
ridazinone), d 48.21 (–CH2NH). Anal. Calcd. for C26H26
N4O3S2: C = 61.64, H = 5.17, N = 11.10, S =
12.71. Found: C = 61.66, H = 5.14, N = 11.08, S =
12.67.
4-(6-Oxo-3-(40-phenoxyphenyl)-5,6-dihydropyridazin-1
(4H)-yl)-N-(benzylcarbamothioyl) benzenesulfonamide
(2f)
Yield = 50%, m.p 186–188°C; IR tmax: 3330, 2955, and
2924 (NH–CS–NH), 1588 (cyclic carbonyl), 1490 (C=S of
1
thiourea), 1377 and 1157 cm-1 (SO2N). H NMR: 2.78
4-(6-Oxo-3-(40-chlorophenyl)-5,6-dihydropyridazin-1
(4H)-yl)-N-(benzylcarbamothioyl) benzenesulfonamide
(2d)
(2H, t, –CH2–CH2), 3.05 (2H, t, –CH2–CH2–), 4.73 (2H, s,
–CH2–C6H5), 7.75-7.90 (6H, m, aromatic protons), 6.99-
7.32 (12H, m, aromatic protons). FAB-MS (m/z): 411
(Base Peak). Anal. Calcd. for C30H26N4O4S2: C = 63.14,
H = 4.59, N = 9.82, S = 11.24. Found: C = 63.09,
H = 4.56, N = 9.81, S = 11.22.
Yield = 45%, m.p 200–202°C; IR tmax: 3320 (NH–CS–
NH), 1671 (cyclic carbonyl), 1639 (C=N), 1585, 1545
(C=S of thiourea), 1335 and 1146 cm-1 (SO2N). 1H NMR:
2.79 (2H, t, –CH2–CH2–), 3.17 (2H, t, –CH2–CH2–), 4.67
(2H, d, –CH2–C6H5), 7.10–7.95 (13H, m, N-phenyl, benzyl
amine, 6-aryl protons), 8.90 (1H, s, –NH–CH2–C6H5),
11.69 (1H, brs s, –NH–SO2). ESI–MS (m/z): 511 (M?-1),
536 (M??Na). 13C NMR (DMSO, d): d 22.16 (–CH2 of
pyridazinone), d 27.35 (–CH2 of pyridazinone), d 47.67
(–CH2NH), d 152.24 (C=N of pyridazinone), d 165.76
(C=O), d 178.52 (C=S). DEPT (DMSO, d): d 22.15 (–CH2
of pyridazinone), d 27.35 (–CH2 of pyridazinone), d 47.67
(–CH2NH). Anal. Calcd. for C24H21ClN4O3S2: C = 56.19,
H = 4.13, N = 10.92, S = 12.50. Found: C = 56.14,
H = 4.09, N = 10.91, S = 12.47.
4-((6-Biphenyl-4-yl) 6-oxo-)-5,6-dihydropyridazin-
1(4H)-yl)-N-(benzylcarbamothioyl)
benzenesulfonamide (2g)
Yield = 52%, m.p 192–194°C; IR tmax: 3316, 3095, and
2922 (NH–CS–NH), 1656 (cyclic carbonyl), 1586 (C=N),
1
1542 (C=S of thiourea), 1327 and 1137 cm-1 (SO2N). H
NMR: 2.81 (2H, t, –CH2–CH2–), 3.21 (2H, t, –CH2–CH2–),
4.68 (2H, s, –CH2–C6H5), 7.10–7.98 (18H, m, aromatic
hydrogens), 8.90 (1H, s, NH–CH2–C6H5), 11.75 (1H, s,
SO2NH). FAB-MS (m/z): 555 (M?1), 556 ((M?2), base
peak).13C NMR (DMSO, d): d 22.22 (–CH2 of pyridazi-
none), d 27.58 (–CH2 of pyridazinone)), d 47.71 (–NH–
CH2), d 153.00 (C=N of pyridazinone), d 165.87 (C=O),
d 178.55 (C=S). DEPT (DMSO, d): d 22.29 (–CH2 of
pyridazinone), d 27.65 (–CH2 of pyridazinone)), d 47.78
(–CH2NH). Anal. Calcd. for C30H26N4O3S2: C = 64.96,
H = 4.72, N = 10.10, S = 11.56. Found: C = 64.98,
H = 4.69, N = 10.13, S = 11.58.
4-(6-Oxo-3-(40-ethylphenyl)-5,6-dihydropyridazin-1
(4H)-yl)-N-(benzylcarbamothioyl) benzenesulfonamide
(2e)
Yield = 60%, m.p.: 201–202°C; IR tmax: 3347, 3067 and
2962 (NH–CS–NH), 1653 (cyclic carbonyl), 1587 (C=N),
1547 (C=S of thiourea), 1330 and 1141 cm-1 (SO2N). H
1
NMR: 1.18 (3H, t, –CH2–CH3), 2.64 (2H, q, –CH2–CH3),
2.76 (2H, t, –CH2–CH2–), 3.14 (2H, t, –CH2–CH2–), 4.67
(2H, d, J = 5.1 Hz, –CH2–C6H5), 7.09–7.26 (5H, m, –CH2–
C6H5), 7.30 (2H, d, J = 8.1 Hz, H-20, H-50), 7.79 (2H, d,
J = 8.1 Hz, H-30, H-50), 7.86 (d, J = 9.00, H-300, H-500),
7.94 (2H, d, J = 8.7 Hz, H-200, H-600), 8.90 (1H, t,
–NH–CH2–C6H5), 11.70 (1H, s, SO2NH). FAB-MS (m/z):
506 (M?), 508 (M??2). 13C NMR (DMSO, d): d 15.40
(–CH2CH3), d 22.25 (–CH2 of pyridazinone), d 27.63
(–CH2CH3), d 27.98 (–CH2 of pyridazinone), d 47.70
(–NH–CH2), d 146.19 (C=N of pyridazinone), d 153.48
(C-40), d 165.90 (C=O of pyridazinone), d 178.00 (C=S).
4-(6-Oxo-3-(40-methoxyphenyl)-5,6-dihydropyridazin-
1(4H)-yl)-N-phenylcarbamothioyl)
benzenesulfonamide (2h)
Yield = 37%, m.p 184–186°C; IR tmax: 3282 (NH–CS–
NH), 1662 (cyclic carbonyl), 1590 (C=N), 1512 and 1494
(C=S of thiourea), 1322 and 1170 cm-1 (SO2N). 1H NMR:
2.73 (2H, t, –CH2–CH2–), 3.11 (2H, t, –CH2–CH2–), 3.79
(3H, s, OCH3), 4.30 (1H, s, –NH–C6H5), 6.71–7.86 (14H,
m, aromatic hydrogens), 6.68 (1H, s, SO2NH). FAB-MS
(m/z): 495 (M??1), 493 (M?-1). Anal. Calcd. for
C24H20N4O4S2: C = 58.28, H = 4.48, N = 11.33,
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