Med Chem Res
(Z)-5-((methyl(3-phenyl-3-(3-(trifluoromethyl)phenoxy)propyl)
amino)methylene)thiazolidine-2,4-dione (3.16) Pale yellow
solid; yield: 90 %; m.p.: 131–132 °C; IR (KBr): tmax 3424,
2927, 2750, 1711, 1671, 1598, 1492, 1451, 1354, 1327,
1291, 1227, 1164, 1124, 1064, 877, 782, 743, 698, 619,
ppm; ESI-HRMS: m/z calcd for C21H22N2O3S ([M?H]?)
383.1398, found 383.1424.
(Z)-5-((methyl(3-phenyl-3-(p-tolyloxy)propyl)amino)
methylene)thiazolidine-2,4-dione (3.20) White solid;
yield: 94 %; m.p.: 127–128 °C; IR (KBr): tmax 3529, 3086,
3010, 2938, 2746, 1672, 1570, 1494, 1435, 1412, 1395,
1277, 1234, 1211, 1161, 1098, 1029, 1002, 976, 946, 920,
1
466 cm-1; H NMR (400 MHz, CDCl3): d 11.60 (s, 1H),
7.58–7.20 (m, 10H), 5.58 (s, 1H), 3.58–3.28 (m, 2H), 3.00
(s, 3H), 2.30–2.04 (m, 2H) ppm; 13C NMR (100 MHz,
CDCl3): d 170.0, 157.5, 143.2, 140.3, 130.5, 130.2, 129.9
(2C), 128.6 (2C), 127.8 (2C), 126.0 (2C), 119.6, 117.2,
112.4, 109.5, 76.9 ppm; ESI-HRMS: m/z calcd for C21-
H19N2O3F3S ([M?H]?) 437.1162, found 437.1141.
854, 829, 758, 736, 699 cm-1 1H NMR (400 MHz,
;
CDCl3): d 11.38 (s, 1H), 7.58 (s, 1H), 7.38–7.20 (m, 5H),
6.98 (d, J = 6.8 Hz, 2H), 6.78 (d, J = 6.8 Hz, 2H), 5.38
(m, 1H), 3.56–3.40 (m, 2H), 3.06 (s, 3H), 2.18 (s, 3H),
2.04–1.98 (m, 2H) ppm; 13C NMR (100 MHz, CDCl3): d
168.6, 167.2, 155.1, 144.4, 141.2, 129.6 (2C), 129.4 (2C),
128.5 (2C), 127.6 (2C), 126.0 (2C), 115.7 (2C), 76.4, 36.6,
20.3 ppm; ESI-HRMS: m/z calcd for C21H22N2O3S
([M?H]?) 383.1398, found 383.1424.
(Z)-5-(((3-hydroxy-3-phenylpropyl)(methyl)amino)methylene)
thiazolidine-2,4-dione (3.17) Off-white solid; yield: 88 %;
m.p.: 107–108 °C; IR (KBr): tmax 3526, 3494, 3085, 3068,
2810, 2743, 1762, 1697, 1669, 1572, 1495, 1277, 1185,
1
1160, 1002, 975, 920, 854, 829, 769, 735, 699 cm-1; H
(Z)-5-((methyl(3-phenylpropyl)amino)methylene)thiazo-
lidine-2,4-dione (3.21) Pale yellow solid; yield: 90 %;
m.p.: 117–118 °C; IR (KBr): tmax 3437, 3027, 2945, 2764,
1718, 1679, 1575, 1445, 1399, 1358, 1348, 1299, 1272,
NMR (400 MHz, CDCl3): d 11.56 (s, 1H), 7.60 (s, 1H),
7.38–7.20 (m, 5H), 5.40 (s, 1H), 4.60 (br.t, J = 7.2 Hz,
1H), 3.44–3.38 (m, 2H), 3.10 (s, 3H), 1.96–1.80 (m, 2H)
ppm; 13C NMR (100 MHz, CDCl3): d 168.7, 167.3, 145.5,
144.5 (2C), 128.0 (2C), 126.8, 125.6 (2C), 85.7, 69.5, 37.6,
30.7 ppm; ESI-HRMS: m/z calcd for C14H16N2O3S
([M?H]?) 293.0936, found 293.0954.
1
1153, 1068, 932, 840, 746, 697, 623, 495, 465 cm-1; H
NMR (400 MHz, CDCl3): d 11.56 (br.s, 1H), 7.60 (s, 1H),
7.38–7.18 (m, 5H), 3.40 (t, J = 5.2 Hz, 2H), 3.10 (s, 3H),
2.62–2.50 (t, J = 7.6 Hz, 2H), 1.90–1.80 (m, 2H) ppm; 13
C
NMR (100 MHz, CDCl3): d 168.5, 167.2, 144.4, 141.0,
128.3 (3C), 128.2 (3C), 125.8, 31.8, 29.5 ppm; ESI-
HRMS: m/z calcd for C14H16N2O2S ([M?H]?) 277.1014,
found 277.1005.
(Z)-5-((methyl(3-phenyl-3-(o-tolyloxy)propyl)amino)
methylene)thiazolidine-2,4-dione (3.18) White solid;
yield: 96 %; m.p.: 129–130 °C; IR (KBr): tmax 3529, 3086,
3009, 2922, 2745, 1672, 1570, 1494, 1452, 1435, 1412,
1396, 1363, 1325, 1277, 1211, 1160, 1098, 1002, 975, 945,
(Z)-5-((4-((2-chlorophenyl)(phenyl)methyl)piperazin-1-yl)
methylene)thiazolidine-2,4-dione (3.22) White solid;
yield: 89 %; m.p.: 92–94 °C; IR (KBr): tmax 3435, 2981,
2955, 2822, 2768, 1715, 1671, 1622, 1581, 1520, 1444,
1390, 1361, 1345, 1281, 1220, 1205, 1183, 1142, 1112,
1
920, 877, 864, 768, 758, 699 cm-1; H NMR (400 MHz,
CDCl3): d 11.60 (br.s, 1H), 7.58 (s, 1H), 7.40–7.22 (m,
5H), 7.18–7.15 (m, 1H), 7.04–6.90 (m, 1H), 6.78–6.66 (m,
2H), 5.40 (br.m, 1H), 4.22 (t, J = 6.6 Hz, 2H), 3.06 (s,
3H), 2.36 (s, 3H), 1.24 (t, J = 6.6 Hz, 2H) ppm; 13C NMR
(100 MHz, CDCl3): d 168.6, 167.2, 155.1, 144.4, 141.2,
129.6 (2C), 129.4 (2C), 128.5 (3C), 127.6, 126.0 (2C),
115.7 (2C), 76.4, 36.6 (2C), 20.0 ppm; ESI-HRMS: m/z
calcd for C21H22N2O3S ([M?H]?) 383.1403, found
383.1424.
1095, 1075, 1043, 967, 916, 838, 739, 639, 554, 452 cm-1
;
1H NMR (400 MHz, CDCl3): d 7.80 (d, J = 8 Hz, 1H),
7.52 (s, 1H), 7.40–7.20 (m, 8H), 4.80 (s, 1H), 3.50 (br.m,
4H), 2.46–2.20 (m, 4H); 13C NMR (100 MHz, CDCl3): d
168.7, 168.6, 142.1, 140.1, 139.2, 132.7, 129.6, 128.7,
128.6, 128.5, 128.1, 127.7, 127.4, 87.5, 69.5, 51.2, 49.6,
45.6, 40.1, 38.8, 11.40; ESI-HRMS m/z: calcd for C21-
H20N3O2SCl ([M?H]?): 414.1057, found 414.1038.
(Z)-5-((methyl(3-phenyl-3-(m-tolyloxy)propyl)amino)
methylene)thiazolidine-2,4-dione (3.19) Off-white
solid; yield: 96 %; m.p.: 119–120 °C; IR (KBr): tmax 3529,
3086, 3010, 2938, 2746, 1672, 1570, 1494, 1435, 1412,
1395, 1277, 1234, 1211, 1161, 1098, 1029, 1002, 976, 946,
(Z)-5-((4-((3-chlorophenyl)(phenyl)methyl)piperazin-1-yl)
methylene)thiazolidine-2,4-dione (3.23) Pale yellow
solid; yield: 95 %; m.p.: 130–131 °C; IR (KBr): tmax 3416,
3024, 2965, 2813, 1710, 1666, 1590, 1492, 1472, 1434,
1361, 1349, 1320, 1250, 1232, 1136, 1099, 1025, 999, 926,
1
920, 854, 829, 758, 736, 699 cm-1; H NMR (400 MHz,
CDCl3): d 8.58 (br.s, 1H), 7.60 (s, 1H), 7.38–7.20 (m, 5H),
7.10–7.04 (m, 1H), 6.78–6.38 (m, 3H), 5.18–5.10 (m, 1H),
3.36–3.22 (m, 2H), 3.10 (s, 3H), 2.30 (s, 3H), 2.18–2.14
(m, 2H) ppm; 13C NMR (100 MHz, CDCl3): d 168.6,
167.2, 155.1, 144.4, 141.2, 129.4 (2C), 128.6 (2C), 128.5
(2C), 127.6 (2C), 126.0 (2C), 115.7, 76.4, 36.6, 20.0 (2C)
1
885, 764, 711, 698, 643, 613, 563, 501, 439 cm-1; H
NMR (400 MHz, CDCl3): d 11.56 (s, 1H), 7.60 (s, 1H),
7.54–7.22 (m, 9H), 4.40 (s, 1H), 3.60–3.54 (m, 4H),
2.38–2.34 (m, 4H) ppm; 13C NMR (100 MHz, CDCl3): d
168.1, 167.6, 144.8, 142.6 (2C), 141.4, 133.2, 130.5 (2C),
123