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6.2.4. (S)-2-((Z)-5-(4-((E)-3-(3-Chlorophenyl)-3-oxoprop-1-en-1-
yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic
acid (6d)
CH]CH), 7.84 (s,1H, CH]), 8.04 (d, J ¼ 15.6 Hz,1H, CH]CH), 7.15e
8.10 (m, 13H, AreH). MS m/z 514 (M þ 1). Anal. Calcd. for
C
29H23NO4S2: C, 67.81; H, 4.51; N, 2.73. Found: C, 67.75; H, 4.55; N,
Yield 83%; m.p.124e125 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
2.69.
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.53 (d, J ¼ 6.0 Hz, 2H, CH2),
5.81 (s, 1H, CH), 7.76 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.81 (s, 1H, CH]),
8.04 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.14e8.21 (m, 13H, AreH). MS m/z
556 (M þ Naþ). Anal. Calcd. for C28H20ClNO4S2: C, 62.97; H, 3.77; N,
2.62. Found: C, 69.99; H, 3.75; N, 2.66.
6.2.11. (S)-2-((Z)-5-(4-((E)-3-(2,4-Dimethylphenyl)-3-oxoprop-1-
en-1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6k)
Yield 86%; m.p.192e193 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
1H NMR (DMSO-d6, 300 MHz, ppm):
d 2.38 (s, 3H, CH3), 2.49 (s, 3H,
6.2.5. (S)-2-((Z)-5-(4-((E)-3-(4-Chlorophenyl)-3-oxoprop-1-en-1-
yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic
acid (6e)
CH3), 3.51 (s, 2H, CH2), 5.89 (s,1H, CH), 7.54 (d, J¼ 15.9 Hz,1H, CH]CH),
7.81 (s, 1H, CH]), 7.92 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.14e7.97 (m, 12H,
AreH), 13.50 (s, 1H, COOH). MS m/z 550 (M þ Naþ). Anal. Calcd. for
C30H25NO4S2: C, 68.29; H, 4.78; N, 2.65. Found: C, 68.33; H, 4.75; N,
2.70.
Yield 24%; m.p. 210e211 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.52 (d, J ¼ 5.4 Hz, 2H, CH2), 5.91
(s,1H, CH), 7.75 (d, J ¼ 15.6 Hz,1H, CH]CH), 7.84 (s,1H, CH]), 8.04 (d,
J ¼ 15.6 Hz, 1H, CH]CH), 7.16e8.22 (m, 13H, AreH), 13.55 (s, 1H,
COOH). MS m/z 578 (M þ Naþ). Anal. Calcd. for C28H20ClNO4S2: C,
62.97; H, 3.77; N, 2.62. Found: C, 62.93; H, 3.79; N, 2.70.
6.2.12. (S)-2-((Z)-5-(4-((E)-3-(2-Methoxyphenyl)-3-oxoprop-1-en-
1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6l)
Yield 51%; m.p. 78e79 ꢀC. IR(KBr)cmꢂ1:3449(OH),1687(C]O).1H
6.2.6. (S)-2-((Z)-5-(4-((E)-3-(2,4-Dichlorophenyl)-3-oxoprop-1-
en-1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6f)
NMR (DMSO-d6, 300 MHz, ppm): d 3.51 (s, 2H, CH2), 3.86 (s, 3H, OCH3),
5.88 (s,1H, CH), 7.35 (d, J ¼ 15.0 Hz, 1H, CH]CH), 7.82 (s,1H, CH]), 7.90
(d, J ¼ 15.6 Hz, 1H, CH]CH), 7.03e7.97 (m, 13H, AreH), 13.44 (s, 1H,
COOH). MS m/z 530 (M þ 1). Anal. Calcd. for C29H23NO5S2: C, 65.77; H,
4.38; N, 2.64. Found: C, 65.80; H, 4.33; N, 2.68.
Yield 52%; m.p. 176e177 ꢀC. IR (KBr) cmꢂ1: 3449 (OH), 1687 (C]
O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d 3.56 (s, 2H, CH2), 5.74 (s,
1H, CH), 7.46 (d, J ¼ 16.2 Hz, 1H, CH]CH), 7.77 (s, 1H, CH]), 7.91 (d,
J ¼ 15.6 Hz, 1H, CH]CH), 7.14e7.96 (m, 12H, AreH). MS m/z 568
(M þ 1). Anal. Calcd. for C28H19Cl2NO4S2: C, 59.16; H, 3.37; N, 2.46.
Found: C, 59.22; H, 3.38; N, 2.45.
6.2.13. (S)-2-((Z)-5-(4-((E)-3-(3-Methoxyphenyl)-3-oxoprop-1-en-
1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6m)
Yield 43%; m.p. 90e91 ꢀC. IR (KBr) cmꢂ1:3449(OH),1687(C]O).1H
6.2.7. (S)-2-((Z)-5-(4-((E)-3-(2-Bromophenyl)-3-oxoprop-1-en-1-
yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic
acid (6g)
NMR (DMSO-d6, 300 MHz, ppm): d 3.51 (s, 2H, CH2), 3.85 (s, 3H, OCH3),
5.89 (s,1H, CH), 7.57 (d, J¼ 15.6 Hz,1H, CH]CH), 7.84 (s,1H, CH]), 8.01
(d, J ¼ 15.9 Hz, 1H, CH]CH), 7.17e8.07 (m, 13H, AreH), 13.46 (s, 1H,
COOH). MS m/z 530 (M þ 1). Anal. Calcd. for C29H23NO5S2: C, 65.77; H,
4.38; N, 2.64. Found: C, 65.75; H, 4.40; N, 2.59.
Yield 68%; m.p.112e113 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.49 (d, J ¼ 5.1 Hz, 2H, CH2), 5.88
(s,1H, CH), 7.40 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.81 (s, 1H, CH]), 7.76 (d,
J ¼ 15.9 Hz, 1H, CH]CH), 7.13e7.93 (m, 13H, AreH), 13.49 (s, 1H,
COOH). MS m/z 580 (M þ Naþ). Anal. Calcd. for C28H20BrNO4S2: C,
58.13; H, 3.48; N, 2.42. Found: C, 58.09; H, 3.51; N, 2.39.
6.2.14. (S)-2-((Z)-5-(4-((E)-3-(4-Methoxyphenyl)-3-oxoprop-1-en-
1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6n)
Yield 46%; m.p.119e120 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
6.2.8. (S)-2-((Z)-5-(4-((E)-3-(3-Bromophenyl)-3-oxoprop-1-en-1-
yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic
acid (6h)
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.53 (d, J ¼ 6.3 Hz, 2H, CH2),
3.88 (s, 3H, OCH3), 5.80 (s, 1H, CH), 7.70 (d, J ¼ 15.6 Hz, 1H, CH]CH),
7.81 (s, 1H, CH]), 8.04 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.01e8.20 (m,13H,
AreH). MS m/z 530 (M þ 1). Anal. Calcd. for C29H23NO5S2: C, 65.77; H,
4.38; N, 2.64. Found: C, 65.79; H, 4.41; N, 2.63.
Yield 31%; m.p.198e199 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.51 (d, J ¼ 5.7 Hz, 2H, CH2), 5.88
(s,1H, CH), 7.74 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.82 (s,1H, CH]), 8.02 (d,
J ¼ 15.9 Hz, 1H, CH]CH), 7.15e8.32 (m, 13H, AreH), 13.45 (s, 1H,
COOH). MS m/z 580 (M þ Naþ). Anal. Calcd. for C28H20BrNO4S2: C,
58.13; H, 3.48; N, 2.42. Found: C, 58.20; H, 3.52; N, 2.33.
6.2.15. (S)-2-((Z)-5-(4-((E)-3-(4-Acetamidophenyl)-3-oxoprop-1-
en-1-yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-
phenylpropanoic acid (6o)
Yield 53%;m.p. 295e296 ꢀC. IR (KBr) cmꢂ1:3449(OH),1687(C]O).
6.2.9. (S)-2-((Z)-5-(4-((E)-3-(4-Bromophenyl)-3-oxoprop-1-en-1-
yl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic
acid (6i)
1H NMR (DMSO-d6, 300 MHz, ppm):
d 2.09 (s, 3H, CH3), 3.50 (d,
J ¼ 5.7 Hz, 2H, CH2), 5.85 (s,1H, CH), 7.69 (d, J ¼ 15.3 Hz, 1H, CH]CH),
7.82 (s, 1H, CH]), 8.02 (d, J ¼ 15.6 Hz, 1H, CH]CH), 7.14e8.16 (m,13H,
AreH), 10.33 (s, 1H, NH). MS m/z 557 (M þ 1). Anal. Calcd. for
C30H24N2O5S2: C, 64.73; H, 4.35; N, 5.03. Found: C, 64.79; H, 4.31; N,
5.06.
Yield 41%; m.p. 211e212 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
1H NMR (DMSO-d6, 300 MHz, ppm):
d
3.51 (d, J ¼ 5.4 Hz, 2H, CH2), 5.90
(s,1H, CH), 7.75 (d, J ¼ 15.9 Hz, 1H, CH]CH), 7.85 (s, 1H, CH]), 8.05 (d,
J ¼ 16.0 Hz, 1H, CH]CH), 7.15e8.13 (m, 13H, AreH), 13.65 (s, 1H,
COOH). MS m/z 602 (M þ Naþ). Anal. Calcd. for C28H20BrNO4S2: C,
58.13; H, 3.48; N, 2.42. Found: C, 58.22; H, 3.45; N, 2.42.
6.2.16. (S)-2-((Z)-4-Oxo-5-(4-((E)-3-oxo-3-phenylprop-1-en-1-yl)
benzylidene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid (6p)
Yield 64%; m.p.106e107 ꢀC. IR (KBr) cmꢂ1: 3449 (OH),1687 (C]O).
6.2.10. (S)-2-((Z)-4-Oxo-5-(4-((E)-3-oxo-3-(p-tolyl)prop-1-en-1-yl)
benzylidene)-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid (6j)
Yield 54%; m.p. 229e230 ꢀC. IR (KBr) cmꢂ1: 3449 (OH), 1687
1H NMR (DMSO-d6, 300MHz, ppm):
d3.53 (s, 2H, CH2), 5.90 (s,1H, CH),
7.75 (d, J ¼ 15.6 Hz,1H, CH]CH), 7.85 (s,1H, CH]), 8.05 (d, J ¼ 15.3 Hz,
1H, CH]CH), 7.15e8.19 (m, 14H, AreH). MS m/z 522 (M þ Naþ). Anal.
Calcd. for C28H21NO4S2: C, 67.31; H, 4.24; N, 2.80. Found: C, 67.28; H,
4.22; N, 2.83.
(C]O). 1H NMR (DMSO-d6, 300 MHz, ppm):
d
2.41 (s, 3H, CH3),
3.51 (d, J ¼ 5.7 Hz, 2H, CH2), 5.89 (s, 1H, CH), 7.71 (d, J ¼ 15.6 Hz, 1H,