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Z.-H. Chen et al. / European Journal of Medicinal Chemistry 45 (2010) 5739e5743
CH]CH), 7.40e8.31 (m, 8H, AreH), 13.57 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm): 193.46, 189.37, 167.28, 167.07, 143.48,
Calcd. for C21H14BrNO4S2: C, 51.65; H, 2.89; N, 2.87; S, 13.13. Found:
C, 51.23; H, 2.92; N, 2.48; S, 13.05.
d
135.85, 135.28, 134.80, 132.31, 131.69, 131.02, 130.35, 127.25, 127.11,
125.37, 123.98, 117.21, 47.03. MS m/z 428 (Mþ1). Anal. Calcd. for
C21H14FNO4S2: C, 59.00; H, 3.30; N, 3.28; S, 15.00. Found: C, 58.97;
H, 3.46; N, 3.19; S, 15.1.
5.2.13. 2-((5E)-5-(4-((E)-3-(3-Bromophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5m)
Yield 41%; m.p. 289e290 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 4.53 (s, 2H, CH2),
5.2.8. 2-((5E)-5-(4-((E)-3-(2-Chlorophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5h)
Yield 40%; m.p. 281e282 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
7.53 (d, J ¼ 15.3 Hz, 1H, CH]CH), 7.87 (s, 1H, CH), 8.03 (d,
J ¼ 15.3 Hz, 1H, CH]CH), 7.55e8.36 (m, 8H, AreH), 13.56 (s, 1H,
COOH). 13C NMR (DMSO-d6, 300 MHz, ppm):
d 193.33, 188.20,
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d
4.75 (s, 2H, CH2),
15.3 Hz, 1H, CH]CH), 7.96 (s, 1H, CH), 7.93
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.41e7.98 (m, 8H, AreH), 13.50
(s, 1H, COOH). 13C NMR (DMSO-d6, 300 MHz, ppm):
193.38,
167.19, 167.06, 143.72, 139.83, 137.16, 136.39, 135.32, 132.44, 131.50,
130.40, 128.04, 123.92, 122.83, 47.15. MS m/z 489 (Mþ1). Anal.
Calcd. for C21H14BrNO4S2: C, 51.65; H, 2.89; N, 2.87; S, 13.13.
Found: C, 51.45; H, 2.92; N, 2.63; S, 13.07.
7.39 (d,
J
¼
d
188.34, 167.72, 166.87, 143.36, 138.59, 137.42, 136.25, 135.06,
133.33, 131.67, 130.58, 130.29, 129.39, 124.18, 123.16, 45.59.
MS m/z 444 (Mþ1). Anal. Calcd. for C21H14ClNO4S2: C, 56.82;
H, 3.18; N, 3.16; S, 14.45. Found: C, 56.76; H, 3.25; N, 3.10; S,
14.40.
5.2.14. 2-((5E)-5-(4-((E)-3-(4-Bromophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5n)
Yield 36%; m.p. 286e287 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 4.75 (s, 2H, CH2), 7.75
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.94 (s, 1H, CH), 8.04 (d, J ¼ 15.3 Hz, 1H,
5.2.9. 2-((5E)-5-(4-((E)-3-(3-Chlorophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5i)
Yield 36%; m.p. 286e287 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
CH]CH), 7.78e8.14 (m, 8H, AreH), 13.58 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm):
d 193.28, 188.27, 167.16, 167.11, 143.72,
139.28, 137.08, 136.36, 135.35, 132.44, 131.52, 130.43, 128.09, 123.93,
122.85, 47.35. MS m/z 489 (Mþ1). Anal. Calcd. for C21H14BrNO4S2:
C, 51.65; H, 2.89; N, 2.87; S,13.13. Found: C, 51.27; H, 2.96; N, 2.53; S,
13.03.
(C]O). 1H NMR (DMSO-d6, 300 M Hz, ppm):
d 4.52 (s, 2H, CH2), 7.60
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.88 (s, 1H, CH), 7.78 (d, J ¼ 15.3 Hz, 1H,
CH]CH), 7.62e8.24 (m, 8H, AreH), 13.55 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm): d 192.36, 187.38, 166.71, 165.80, 143.32,
138.75, 137.48, 136.43, 135.03, 133.31, 131.64, 130.97, 130.28, 129.36,
124.14, 123.25, 45.68. MS m/z 444 (Mþ1). Anal. Calcd. for
C21H14ClNO4S2: C, 56.82; H, 3.18; N, 3.16; S, 14.45. Found: C, 56.80;
H, 3.29; N, 3.06; S, 14.63.
5.2.15. 2-((5E)-5-(4-((E)-3-(3-Fluorophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5o)
Yield 36%; m.p. 262e263 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d
4.50 (s, 2H, CH2),
15.3 Hz, 1H, CH]CH), 7.97 (s, 1H, CH), 7.82
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.36e8.03 (m, 8H, AreH), 13.56
(s, 1H, COOH). 13C NMR (DMSO-d6, 300 MHz, ppm):
193.25,
7.55 (d,
J
¼
5.2.10. 2-((5E)-5-(4-((E)-3-(4-Chlorophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5j)
Yield 44%; m.p. 284e285 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
d
189.16, 167.45, 167.09, 143.47, 135.88, 135.34, 134.90, 132.41,
131.61, 131.05, 130.18, 127.69, 127.22, 125.38, 123.96, 117.38, 47.06.
MS m/z 428 (Mþ1). Anal. Calcd. for C21H14FNO4S2: C, 59.00;
H, 3.30; N, 3.28; S, 15.00. Found: C, 59.09; H, 3.46; N, 3.17; S,
15.11.
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 4.76 (s, 2H, CH2), 7.78
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.95 (s, 1H, CH), 8.06 (d, J ¼ 15.3 Hz, 1H,
CH]CH), 7.65e8.23 (m, 8H, AreH), 13.45 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm): d 193.36, 188.36, 167.70, 166.80, 143.33,
138.79, 137.42, 136.45, 135.03, 133.32, 131.62, 130.98, 130.29, 129.39,
124.10, 123.27, 45.64. MS m/z 444 (Mþ1). Anal. Calcd. for
C21H14ClNO4S2: C, 56.82; H, 3.18; N, 3.16; S, 14.45. Found: C, 56.73;
H, 3.10; N, 3.29; S, 14.56.
5.2.16. 2-((5E)-5-(4-((E)-3-(4-Nitrophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5p)
Yield 39%; m.p. 293e294 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 4.75 (s, 2H, CH2), 7.76
5.2.11. 2-((5E)-5-(4-((E)-3-(2,4-Dichlorophenyl)-3-oxoprop-1-
enyl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5k)
Yield 53%; m.p. 235e236 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.94 (s, 1H, CH), 8.07 (d, J ¼ 15.3 Hz, 1H,
CH]CH), 7.79e8.39 (m, 8H, AreH), 13.56 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm): d 193.35, 188.63, 169.67, 167.59, 166.76,
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d
4.75 (s, 2H, CH2), 7.43
150.35, 144.31, 142.51, 137.20, 135.25, 133.31, 131.64, 130.42, 124.33,
124.11, 123.39, 45.47. MS m/z 455 (Mþ1). Anal. Calcd. for
C21H14N2O6S2: C, 55.50; H, 3.10; N, 6.16; S, 14.11. Found: C, 55.28; H,
3.45; N, 6.03; S, 14.07.
(d, J ¼ 15.3 Hz, 1H, CH]CH), 7.96 (s, 1H, CH), 7.80 (d, J ¼ 15.3 Hz, 1H,
CH]CH), 7.38e7.99 (m, 7H, AreH), 13.50 (s, 1H, COOH). 13C NMR
(DMSO-d6, 300 MHz, ppm): d 193.37, 192.62, 167.71, 166.78, 145.44,
137.59, 136.88, 136.33, 135.40, 133.24, 131.82, 131.67, 130.28, 128.16,
123.57, 45.52. MS m/z 479 (Mþ1). Anal. Calcd. for C21H13Cl2NO4S2:
C, 52.73; H, 2.74; N, 2.93; S, 13.41. Found: C, 52.48; H, 2.92; N, 2.63;
S, 13.27.
5.2.17. 2-((5E)-5-(4-((E)-3-(3-(Methoxymethoxy)phenyl)-3-
oxoprop-1-enyl)benzylid-ene)-4-oxo-2-thioxothiazolidin-3-yl)
acetic acid (5q)
Yield 46%; m.p. 292e293 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
5.2.12. 2-((5E)-5-(4-((E)-3-(2-Bromophenyl)-3-oxoprop-1-enyl)
benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5l)
Yield 32%; m.p. 281e282 ꢁC. IR (KBr) cmꢂ1: 3449 (OH), 1687
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 3.16 (s, 3H, OCH3),
4.57 (s, 2H, CH2), 5.31 (s, 2H, OCH2), 7.35 (d, J ¼ 15.3 Hz, 1H,
CH]CH), 7.97 (s, 1H, CH), 7.70 (d, J ¼ 15.3 Hz, 1H, CH]CH),
7.33e8.10 (m, 8H, AreH), 13.54 (s, 1H, COOH). 13C NMR (DMSO-d6,
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 4.75 (s, 2H, CH2),
7.51 (d, J ¼ 15.3 Hz, 1H, CH]CH), 7.95 (s, 1H, CH), 7.92 (d,
300 MHz, ppm): d 193.44, 187.88, 167.52, 166.89, 161.23, 142.34,
J ¼ 15.3 Hz, 1H, CH]CH), 7.36e8.02 (m, 8H, AreH), 13.58 (s, 1H,
136.63, 134.37, 133.25, 131.68, 131.39, 130.17, 130.18, 124.46, 123.33,
116.33, 94.18, 56.35, 46.08. MS m/z 470 (Mþ1). Anal. Calcd. for
C23H19NO6S2: C, 58.83; H, 4.08; N, 2.98; S, 13.66. Found: C, 58.79;
H, 4.37; N, 2.72; S, 13.46.
COOH). 13C NMR (DMSO-d6, 300 MHz, ppm):
d 193.35, 188.40,
167.18, 167.06, 143.72, 139.83, 137.16, 136.39, 135.82, 132.74, 131.55,
130.40, 128.04, 123.93, 122.86, 47.19. MS m/z 489 (Mþ1). Anal.