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M. P. Gauthier et al. / Bioorg. Med. Chem. 14 (2006) 918–927
133.26 (C1-Ph-N), 134.42 (C1-Ph), 137.90 (2C, C3C5-
Ph-N), 172.71 (CO), 182.51 (CS). IR (KBr): 3159 (m
NH), 1756 (m C@O), 1585 (m C–C), 1522 (thioureide),
1405 (mas NCS), 1276–1245 (ms NCS) cmꢁ1. Anal. Calcd
for C15H11IN2OS: C, 45.70; H, 2.81; N, 7.11; S, 8.13.
Found: C, 46.22; H, 2.68; N, 7.29; S, 7.52.
129.21 (2C, C2C6-Ph), 129.76 (2C, C3C5-Ph-N),
134.35 (C1-Ph), 136.28 (C4-Ph-N), 144.32 (C1-Ph-N),
172.70 (CO), 182.32 (CS). IR (KBr): 3360 (m NHsulfo),
3063–3043 (m NH), 1759 (m C@O), 1596 (m C–C), 1512
(thioureide), 1406 (mas NCS), 1269 (ms NCS) cmꢁ1. Anal.
Calcd for C15H13N3O3S2: C, 51.86; H, 3.77; N, 12.10; S,
18.46. Found: C, 51.61; H, 3.76; N, 11.97; S, 18.18.
5.1.1.12.
( )5-Phenyl-2-thioxo-3-[4-(trifluorometh-
yl)phenyl]imidazolidin-4-one (12). Yield: 42%. Mp: 223–
224 ꢁC. 1H NMR (DMSO-d6) d ppm: d 5.62 (s, 1H,
CH-CO), 7.45 (s, 5H, Ph), 7.63 (d, 2H, 2H-Ph and
6H-Ph, J = 8.10 Hz), 7.90 (d, 2H, 3H-Ph and 5H-Ph,
J = 8.60 Hz), 11.12 (s, 1H, NH). 13C NMR (DMSO-
d6) d ppm: 62.91 (C5-heterocycle), 125.59 (CF3),
127.31 (2C, C3C5-Ph), 128.83 (2C, C2C6-Ph-N),
128.97 (C4-Ph), 129.19 (2C, C2C6-Ph), 129.71 (C4-Ph-
N), 129.86 (2C, C3C5-Ph-N), 134.13 (C1-Ph), 136.94
(C1-Ph-N), 172.36 (CO), 181.95 (CS). IR (KBr): 3158
(m NH), 1759 (m C@O), 1615 (m C–C), 1526 (thioureide),
1406 (mas NCS), 1274–1246 (ms NCS) cmꢁ1. Anal. Calcd
for C16H11F3N2 OS: C, 57.14; H, 3.30; N, 8.33; S, 9.53.
Found: C, 57.47; H, 3.49; N, 8.51; S, 9.57.
5.1.1.16. ( )3-(3-Methylphenyl)-5-phenyl-2-thioxoimi-
dazolidin-4-one (16). Yield: 47%. Mp: 218–219 ꢁC. H
1
NMR (DMSO-d6) d ppm: 2.34 (s, 3H, CH3), 5.59 (d,
1H, CH-CO, J = 1.32 Hz), 7.12–7.46 (m, 9H, 2 Ph),
10.9 (s, 1H, NH). 13C NMR (DMSO-d6) d ppm: 20.76
(CH3), 62.81 (C5-heterocycle), 126.13 (C6-Ph-N),
127.30 (2C, C3C5-Ph), 128.81 (C2-Ph-N), 129.00 (C4-
Ph), 129.22 (2C, C2C6-Ph), 129.37 (C4-Ph-N), 129.61
(C5-Ph-N), 133.44 (C3-Ph-N), 134.63 (C1-Ph), 138.54
(C1-Ph-N), 172.77 (CO), 183.05 (CS). IR (KBr): 3174
(m NH), 1757 (m C@O), 1609–1591 (m C–C), 1518 (thio-
ureide), 1402 (mas NCS), 1274–1254 (ms NCS) cmꢁ1. Anal.
Calcd for C16H14N2OS: C, 68.06; H, 5.00; N, 9.92; S,
11.36. Found: C, 67.82; H, 5.33; N, 10.14; S, 11.40.
5.1.1.13. ( )3-(4-Nitrophenyl)-5-phenyl-2-thioxoimi-
dazolidin-4-one (13). Yield: 25%. Mp: 181–182 ꢁC. H
5.1.1.17. ( )3-(3-Methoxyphenyl)-5-phenyl-2-thioxo-
imidazolidin-4-one (17). Yield: 26%. Mp: 197–199 ꢁC.
1H NMR (DMSO-d6) d ppm: 3.77 (s, 3H, CH3), 5.57
(s, 1H, CH-CO), 6.85–7.09 (m, 3H, Ph), 7.32–7.50 (m,
6H, Ph), 10.9 (s, 1H, NH). d ppm: 55.44 (CH3), 62.83
(C5-heterocycle), 114.48 (C2-Ph-N), 114.93 (C4-Ph-N),
121.18 (C6-Ph-N), 127.30 (C5-Ph-N), 127.36 (2C,
C3C5-Ph), 128.97 (C4-Ph), 129.18 (2C, C2C6-Ph),
129.72 (C1-Ph-N), 134.56 (C1-Ph), 159.62 (C3-Ph-N),
172.82 (CO), 182.90 (CS). IR (KBr): 3159 (m NH),
1754 (m C@O), 1607 (m C–C), 1518 (thioureide), 1404
(mas NCS), 1272 (ms NCS) cmꢁ1. Anal. Calcd for
C16H14N2O2S: C, 64.41; H, 4.73; N, 9.39; S, 10.75.
Found: C, 64.42; H, 5.01; N, 9.58; S, 10.56.
1
NMR (DMSO-d6) d ppm: 5.63 (d, 1H, CH-CO,
J = 1.10 Hz), 7.45 (s, 5H, Ph), 7.71 (d, 2H, 2H-Ph and
6H-Ph, J = 9.01 Hz), 8.36 (d, 2H, 3H-Ph and 5H-Ph,
J = 9.23 Hz), 11.2 (s, 1H, NH). 13C NMR (DMSO-d6)
d ppm: 63.15 (C5-heterocycle), 124.18 (2C, C2C6-Ph-
N), 127.48 (2C, C3C5-Ph), 129.13 (C4-Ph), 129.22 (2C,
C2C6-Ph), 130.46 (2C, C3C5-Ph-N), 134.23 (C1-Ph),
139.11 (C4-Ph-N), 147.35 (C1-Ph), 172.49 (CO),
181.85 (CS). IR (KBr): 3178 (m NH), 1766 (m C@O),
1614–1595 (m C–C), 1535 (thioureide), 1403 (mas NCS),
1246 (ms NCS) cmꢁ1. Anal. Calcd for C15H11N3O3S: C,
57.50; H, 3.54; N, 13.41; S, 10.23. Found: C, 57.72; H,
3.94; N, 13.44; S, 9.85.
5.1.1.18. ( )3-(3-Fluorophenyl-5-phenyl)-2-thioxoimi-
1
5.1.1.14. ( )3-[4-(Methylsulfonyl)phenyl]-5-phenyl-2-
thioxoimidazolidin-4-one (14). Yield: 15%. Mp: 280–
281 ꢁC. 1H NMR (DMSO-d6) d ppm: d 3.30 (s, 3H,
CH3), 5.62 (s, 1H, CH-CO), 7.42–7.47 (m, 5H, Ph),
7.68 (d, 2H, 2H-Ph and 6H-Ph, J = 8.80 Hz), 8.06 (d,
2H, 3H-Ph and 5H-Ph, J = 8.40 Hz), 11.2 (s, 1H, NH).
d ppm: 43.77 (CH3), 63.10 (C5-heterocycle), 127.46
(2C, C3C5-Ph), 127.90, (2C, C2C6-Ph-N), 129.13 (C4-
Ph), 129.22 (2C, C2C6-Ph), 130.15 (2C, C3C5-Ph-N),
134.31 (C1-Ph), 137.88 (C4-Ph-N), 141.02 (C1-Ph-N),
172.64 (CO), 182.09 (CS). IR (KBr): 3305 (m NHsulfo),
3022–3005 (m NH), 1755 (m C@O), 1596 (m C–C), 1509
(thioureide), 1403 (mas NCS), 1252 (ms NCS) cmꢁ1. Anal.
Calcd for C16H14N2O3 S2: C, 55.47; H, 4.07; N, 8.09; S,
18.51. Found: C, 54.68; H, 3.87; N, 8.10; S, 18.31.
dazolidin-4-one (18). Yield: 35%. Mp: 223–224 ꢁC. H
NMR (DMSO-d6) d ppm: 5.58 (s, 1H, CH-CO), 7.03–
7.59 (m, 9H, 2 Ph), 11.0 (s, 1H, NH). 13C NMR
(DMSO-d6) d ppm: 62.86 (C5-heterocycle), 111.28 (C2-
Ph-N), 113.87 (C4-Ph-N), 115.42 (C6-Ph-N), 127.49
(2C, C3C5-Ph), 129.03 (C4-Ph), 129.17 (2C, C2C6-Ph),
133.98 (C5-Ph-N), 134.47 (C1-Ph), 137.13 (C1-Ph-N),
161.21 (C3-Ph-N), 172.91 (CO), 182.51 (CS). IR (KBr):
3180 (m NH), 1760 (m C@O), 1600 (m C–C), 1518 (thioure-
ide), 1405 (mas NCS), 1276–1254 (ms NCS) cmꢁ1. Anal.
Calcd for C15H11FN2OS: C, 62.92; H, 3.87; N, 9.78; S,
11.20. Found: C, 63.28; H, 4.21; N, 9.99; S, 11.09.
5.1.1.19. ( )3-(3-Chlorophenyl)-5-phenyl-2-thioxoimi-
1
dazolidin-4-one (19). Yield: 23%. Mp: 201–202 ꢁC. H
NMR (DMSO-d6) d ppm: 5.58 (s, 1H, CH-CO), 7.32–
7.57 (m, 9H, 2 Ph), 11.1 (s, 1H, NH). d ppm: 62.99
(C5-heterocycle), 123.82 (C6-Ph-N), 125.99 (C2-Ph-N),
127.51 (2C, C3C5-Ph), 128.05 (C4-Ph-N), 129.03 (C4-
Ph), 129.15 (2C, C2C6-Ph), 130.57 (C5-Ph-N), 132.98
(C3-Ph-N), 134.38 (C1-Ph), 134.83 (C1-Ph-N), 172.69
(CO), 182.42 (CS). IR (KBr): 3161 (m NH), 1766 (m
C@O), 1592 (m C–C), 1519 (thioureide), 1399 (mas
NCS), 1276–1244 (ms NCS) cmꢁ1. Anal. Calcd for
5.1.1.15. ( )3-[4-(Aminosulfonyl)phenyl]-5-phenyl-2-
thioxoimidazolidin-4-one (15). Yield: 25%. Mp:
>350 ꢁC. 1H NMR (DMSO-d6) d ppm: 5.63 (s, 1H,
CH-CO), 7.42–7.50 (m, 7H, Ph and NH2), 7.58 (d, 2H,
2H-Ph and 6H-Ph, J = 8.00 Hz), 7.94 (d, 2H, 3H-Ph
and 5H-Ph, J = 8.40 Hz), 11.1 (s, 1H, NH). 13C NMR
(DMSO-d6) d ppm: 63.02 (C5-heterocycle), 126.43 (2C,
C2C6-Ph-N), 127.38, (2C, C3C5-Ph), 129.08 (C4-Ph),