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A. S. Aboraia et al. / Bioorg. Med. Chem. 14 (2006) 1236–1246
5H), 7.90 (d, 1H; J ꢁ 8 Hz), 8.50 (s, 1H). Anal. Calcd
for C15H12ClN3O2S: C, 53.98; H 3.62; N, 12.59. Found:
C, 53.88; H, 3.36, N, 12.66.
7.90–8.30 (m, 4H), 10.50 (s, 1H). Anal. Calcd for
C16H13N3O4S: C, 55.97; H, 3.82; N, 12.24. Found: C,
55.58; H, 3.70; N, 12.24.
4.1.2.12. 3-[(4-Bromoanilino)methyl]-5-(2-hydroxyphe-
nyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (3l). Recrys-
tallization from ethanol; yield: 80%; mp: 192–194 ꢁC
(reported 160 ꢁC)13; IR (KBr), mmax/cmꢀ1: 3545–3235
(OH and NH), 1621 (C@N), 1593 (C@C), 1424 (C@S),
4.1.2.17.
1-[4-([5-(2-Hydroxyphenyl)-2-thioxo-2,3-
dihydro-1,3,4-oxadiazol-3-yl]methyl amino)phenyl]-1-eth-
anone (3q). Recrystallization from aq ethanol; yield:
82%; mp: 206–208 ꢁC; IR (KBr), mmax/cmꢀ1: 3550–3227
(OH and NH), 1653 (C@O), 1618 (C@N), 1594
(C@C), 1425 (C@S), 1237 and 1181 (C–O–C), 821,
1
1260 and 1123 (C–O–C), 815, 740; H NMR (DMSO-
1
d6), d ppm: 5.7 (s, 3H), 6.75–7.25 (m, 2H), 7.25–7.75
(m, 5H), 7.90 (d, 1H; J ꢁ 8 Hz), 8.50 (s, 1H). Anal.
758; H NMR (DMSO-d6), d ppm: 2.55 (s, 3H), 5.70
(d, 2H; J ꢁ 7), 6.80–7.40 (m, 4H), 7.40–8.35 (m, 5H),
1
Calcd for C15H12BrN3O2S: C, 47.63; H, 3.20; N,
11.11. Found: C, 47.97; H 3.07; N, 10.90.
10.80 (s, 1H). Anal. Calcd for C17H15N3O3S ꢂ H2O: C,
58.27; H, 4.60; N,12.04. Found: C, 58.34; H,24.53; N,
12.01.
4.1.2.13. 5-(2-Hydroxyphenyl)-3-[(3-nitroanilino)meth-
yl]-2,3-dihydro-1,3,4-oxadiazole-2-thione (3m). Recrys-
tallization from ethanol; yield: 80%; mp: 214–216 ꢁC
(reported 200 ꢁC)13. IR (KBr), mmax/cmꢀ1: 3550–3245
(OH and NH), 1621 (C@N), 1595 (C@C), 1525 and
1386 (NO2), 1427 (C@S), 1249 and 1103 (C–O–C),
4.1.2.18.
2-Hydroxy-4-([5-(2-hydroxyphenyl)-2-thi-
oxo-2,3-dihydro-1,3,4-oxadiazol-3-yl]methylamino)benzoic
acid (3r). Recrystallization from ethanol; yield: 84%;
mp: 197–199 ꢁC; IR (KBr), mmax/cmꢀ1: 3550–3125
(OH, NH and COOH), 1644 (C@O), 1620 (C@N),
1591 (C@C), 1428 (C@S), 1251 and 1101 (C–O–C),
1
850, 755, 749,; H NMR (DMSO-d6), d ppm: 5.90 (d,
1
2H; J ꢁ 8.0 Hz), 7.00–8.10 (m, 8H), 8.20 (d, 1H;
J ꢁ 8.0 Hz), 11.00 (s, 1H). Anal. Calcd for,
C15H12N4O4S: C, 52.32; H, 3.51; N, 16.27. Found: C,
52.02; H, 3.57; N, 16.32.
859, 773, 692; H NMR (DMSO-d6), d ppm: 5.46 (s,
2H), 6.42–6.45 (m, 2H), 6.95 (dd, 1H; J ꢁ 7.3, 7.7 Hz),
7.03 (d, 1H; J ꢁ 7.9 Hz), 7.43 (ddd, 1H; J ꢁ 1.7, 7.3,
8.8 Hz), 7.52 (d, 1H; J ꢁ 9.2 Hz), 7.62 (dd, 1H;
J ꢁ 1.7, 7.9 Hz), 7.90 (t, 1H; J ꢁ 7.0, 14 Hz), 10.50 (s,
1H), 11.40 (s, 1H), 13.10 (br s, 1H); 13C NMR
(DMSO-d6), d ppm: 56.8, 98.5, 102.5, 105.8, 108.7,
117, 119.4, 129.1, 131.3, 133.8, 152.3, 156.4, 158.2,
163.3, 171.9, 175.1. Anal. Calcd for C16H13N3O5S: C,
53.48; H, 3.65; N, 11.69. Found: C, 53.22; H, 3.65; N,
11.45.
4.1.2.14. 5-(2-Hydroxyphenyl)-3-[(4-nitroanilino)meth-
yl]-2,3-dihydro-1,3,4-oxadiazole-2-thione (3n). Recrystal-
lization from ethanol; yield: 79%; mp: 209–210 ꢁC
(reported 210 ꢁC).13 IR (KBr), mmax/cmꢀ1: 3545–3245
(OH and NH), 1620 (C@N), 1592 (C@C), 1524 and
1343 (NO2), 1427 (C@S), 1261 and 1088 (C–O–C),
1
864, 755; H NMR (DMSO-d6), d ppm: 5.75 (d, 2H;
J ꢁ 8.0 Hz), 7.00 (d, 1H; J ꢁ 8.0 Hz), 7.20 (d, 1H;
J ꢁ 8.0 Hz), 7.40–7.70 (m, 4H), 7.85 (d, 1H; J ꢁ 8.0 Hz),
8.00 (m, 2H), 10.80 (s, 1H). Anal. calcd. for,
C15H12N4O4S: C, 52.32; H, 3.51; N, 16.27. Found: C,
52.04; H, 3.52; N, 16.43.
4.1.2.19.
3-[(Ethylanilino)methyl]-5-(2-hydroxyphe-
nyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (3s). Recrys-
tallization from aq ethanol; yield: 85%; mp: 152–
154 ꢁC; IR (KBr), mmax/cmꢀ1: 3550–3300 (OH), 1632
(C@N), 1596 (C@C), 1423 (C@S), 1251 and 1095 (C–
1
O–C), 755, 732, 695; H NMR (CDCl3), d ppm: 1.30
4.1.2.15. 2-([5-(2-Hydroxyphenyl)-2-thioxo-2,3-dihy-
dro-1,3,4-oxadiazol-3-yl]methyl amino)benzoic acid (3o).
Recrystallization from ethanol; yield: 82%; mp: 202–
204 ꢁC; IR (KBr), mmax/cmꢀ1: 3550–3255 (OH, NH and
COOH), 1673 (C@O), 1622 (C@N), 1595 (C@C), 1424
(C@S), 1263 and 1176 (C–O–C), 756;1H NMR
(DMSO-d6), d ppm: 5.66 (d, 2H; J ꢁ 7.2 Hz), 6.73 (dd,
1H; J ꢁ 1.0, 7.6 Hz), 6.90 (dd, 1H; J ꢁ 7.3, 7.5), 7.00
(dd, 1H; J ꢁ 4.7, 8.3 Hz), 7.22 (d, 1H; J ꢁ 8.4 Hz),
7.32-7.45 (m, 2H), 7.62 (dd, 1H; J ꢁ 7.9, 9.5 Hz), 7.84
(d, 1H; J ꢁ 7.9 Hz), 8.86 (t, 1H; J ꢁ 7.2, 14.5 Hz),
10.50 (s, 1H), 12.94 (br s, 1H). Anal. Calcd for
C16H13N3O4S: C, 55.97; H, 3.82; N, 12.24. Found: C,
55.69; H, 4.32; N, 12.12.
(t, 3H), 3.70 (q, 2H), 5.80 (s, 2H), 6.75–7.60 (m, 8H),
7.70 (d, 1H; J ꢁ 9.0 Hz), 7.90 (d, 1H; J ꢁ 8 Hz). Anal.
1
Calcd for C17H17N3O2S ꢂ H2O: C, 57.61; H, 5.69; N,
2
11.86. Found: C, 57.93; H, 5.68; N, 12.02.
4.1.2.20. 3-[(Diphenylamino)methyl]-5-(2-hydroxyphe-
nyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione (3t). Recrys-
tallization from ethanol; yield: 70%; mp: 191–193 ꢁC;
IR (KBr), mmax/cmꢀ1: 3550–3260 (OH), 1617 (C@N),
1595 (C@C), 1420 (C@S), 1230 and 1115 (C–O–C),
750, 725, 691; 1H NMR (CDCl3), d ppm: 1.30 (t,
3H), 3.70 (q, 2H), 5.80 (s, 2H), 6.75–7.60 (m, 8H),
7.70 (d, 1H; J ꢁ 9.0 Hz), 7.90 (d, 1H; J ꢁ 8 Hz); 13C
NMR (CDCl3), d ppm: 64.8, 108.6, 116.6, 116.9,
119.2, 121.3, 122.6, 129.1, 133.5, 145.6, 156.4, 158.2,
175.2. MS: 375 [M+]. Anal. Calcd for C21H17N3O2S:
C, 67.18; H, 4.56; N, 11.19. Found: C, 66.92; H,
5.03; N, 11.16.
4.1.2.16. 4-([5-(2-Hydroxyphenyl)-2-thioxo-2,3-dihy-
dro-1,3,4-oxadiazol-3-yl]methyl amino)benzoic acid (3p).
Recrystallization from ethanol; yield: 80%; mp: 213–
215 ꢁC (reported 212 ꢁC)13. IR (KBr),
m :
max/cmꢀ1
3550–3245 (OH, NH and COOH), 1674 (C@O), 1613
4.1.2.21.
no)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione
5-(2-Hydroxyphenyl)-3-[(2-pyridylami-
(3u).
(C@N), 1606 (C@C), 1431 (C@S), 1269 and 1185 (C–
1
O–C), 856, 739; H NMR (DMSO-d6), d ppm: 5.75 (d,
Recrystallization from ethanol; yield: 81%; mp: 207–
209 ꢁC; IR (KBr), mmax/cmꢀ1: 3550–3245 (OH and
2H; J ꢁ 8 Hz), 6.8–7.35 (m, 4H), 7.30–7.90 (m, 2H),