446
Md. Mushtaque et al. / European Journal of Medicinal Chemistry 55 (2012) 439e448
2H, J ¼ 7.2 Hz, CH2), 2.40e2.17 (m,1H, CH),1.01 (d, 6H, J ¼ 6.6 Hz, CH
(CH3)2); 13C NMR (CDCl3)
(ppm): 167.35 (C]O), 150.99 (C]N),
(cmꢀ1): 1694 (eNeC]O), 1629 (C]N), 763 (CeSeC), 1370 (tert. N),
1582 (C]C); 1H NMR (CDCl3)
(ppm): 7.44e7.36 (m, 3H, AreH),
d
d
150.99 (SeC]C), 148.49 (C]C), 131.78, 130.53, 129.32, 126.48,
124.67, 121.14, 118.79, 114.49 (aromatic), 55.37 (OCH3), 50.11 (CeN),
26.94 (CH), 20.11 (CH3); TOF MS ESþ m/z: [Mþ] 366 (100%).
7.20 (t, 1H, J ¼ 7.5 Hz, AreH), 7.01 (t, 2H, J ¼ 7.5 Hz, AreH), 6.96
(d, 1H, J ¼ 5.1 Hz, AreH), 7.97 (s, 1H, CH]C), 2.40 (s, 3H, CH3), 3.84
(d, 2H, J ¼ 7.5 Hz, CH2), 2.38e2.26 (m,1H, CH),1.01 (d, 6H, J ¼ 6.9 Hz,
CH(CH3)2); 13C NMR (CDCl3)
d (ppm): 167.15 (C]O), 150.44 (C]N),
4.3.8. (2Z,5Z)-3-(5-Methylbenzylidene)-3-(2-methylpropyl)-2-
(phenylimino)-1,3-thiazolidin-4-one (10)
124.76 (SeC]C), 148.32 (C]C), 142.19, 132.57, 130.97, 129.35,
129.16, 123.50, 122.08, 121.15, 118.85 (aromatic), 50.3 (CeN), 26.99
(CH), 20.1 (CH3), 14.42 (CH3); TOF MS ESþ m/z: [Mþ] 356 (100%).
Yield: 8%; m.p: 104 ꢁC; Anal. calc. C21H22N2O2S: C 68.38, H 6.05, N
6.05, S 8.75%. Found: C 68.79, H 6.02, N 7.61, S 8.75%. IR nmax (cmꢀ1):
1690 (eNeC]O),1620 (C]N), 760 (CeSeC),1371 (tert. N),1559 (C]
4.3.13. (2Z,5Z)-5-(4-Hydroxy-3-methoxybenzylidene)-3-isobutyl-2
(phenylimino)thiazolidin-4-one (15)
C); 1H NMR (CDCl3)
d (ppm): 7.41e7.32 (m, 6H, AreH), 7.00e6.92 (m,
3H, AreH), 7.71 (s,1H, CH]C), 3.84 (d, 2H, J ¼ 7.5 Hz, CH2), 2.43e2.30
Yield: 85%; m.p: 163 ꢁC; Anal. calc. C21H22N2O3S: C 65.95, H 5.80,
N 7.32, S 8.38%. Found: C 66.30, H 6.09, N 7.7, S 7.89%. IR nmax (cmꢀ1):
3513.49 (OH), 1690 (eNeC]O), 1624 (C]N), 756.45 (CeSeC),
(m, 1H, CH), 1.01 (d, 6H, J ¼ 6.6 Hz, CH(CH3)2), 2.28 (s, 3H, CH3); 13
C
NMR (CDCl3)
d (ppm): 167.20 (C]O), 150.04 (C]N), 124.23 (SeC]
C), 148.40 (C]C), 151.65, 133.73, 131.53, 130.32, 129.95, 129.48,
127.14, 126.45 (aromatic), 50.05 (CeN), 26.94 (CH), 23.54 (CH3),
20.01 (CH3)2CH; TOF MS ESþ m/z: [Mþ] 350 (100%).
1363.13 (tert. N), 1579.24 (C]C); 1H NMR (CDCl3)
d (ppm): 7.40
(t, 2H, J ¼ 7.5 Hz, AreH), 7.20e7.15 (m, 1H, AreH), 7.03 (t, 3H,
J ¼ 7.5 Hz, AreH), 6.98 (d, 2H, J ¼ 4.5 Hz, AreH), 7.67 (s, 1H, CH]C),
3.88 (s, 3H, OCH3), 3.84 (d, 2H, J ¼ 7.5 Hz, CH2), 2.39e2.30 (m, 1H,
4.3.9. (2Z,5Z)-5-(2-Hydroxybenzylidene)-3-isobutyl-2-(phenylimino)
thiazolidin-4-one (11)
CH), 1.01 (d, 6H, J ¼ 6.9 Hz, CH (CH3)2); 13C NMR (CDCl3)
d (ppm):
167.10 (C]O), 150.82 (C]N), 124.71 (SeC]C), 148.40 (C]C), 147.4,
146.74, 130.90,129.31, 126.38, 123.89, 121.14, 118.92, 115.06, 112.64
(aromatic), 5 6.02 (OCH3), 50.3 (CeN), 26.96 (CH), 20.12 (CH), 15.12
(CH3); TOF MS ESþ m/z: [Mþ] 382 (100%).
Yield: 85%; m.p: 213 ꢁC; Anal. calc. C20H20N2O2S: C 68.16, H 5.72,
N 7.95, S 9.10%. Found: C 68.13, H 5.72, N7.91, S 9.05%. IR nmax
(cmꢀ1): 3510 (OH), 1675 (eNeC]O), 1623 (C]N), 745 (CeSeC),
1339 (tert. N), 1582 (C]C); 1H NMR (CDCl3)
d (ppm): 7.38e7.33
(t, 3H, J ¼ 7.2 Hz, AreH), 7.22e7.15 (m, 2H, AreH), 7.00 (d, 2H,
J ¼ 8.1 Hz, AreH), 6.91e6.87 (m, 2H, AreH), 8.30 (s, 1H, OH), 7.40 (s,
1H, CH]C), 3.87 (d, 2H, J ¼ 7.5 Hz, CH2), 2.40e2.31 (m, 1H, CH), 1.02
4.3.14. (2Z,5Z)-5-(3-Chlorobenzylidene)-3-isobutyl-2-(phenylimino)
thiazolidin-4-one (16)
Yield: 85%; m.p: 145 ꢁC; Anal calc. C20H19ClN2OS: C 64.77, H 5.16,
N 7.55, S 8.64%. Found: C 64.53, H 5.58, N7.93, S 8.60%. IR nmax
(cmꢀ1): 1701 (eNeC]O), 1612 (C]N), 768 (CeSeC), 1374 (tert. N),
(d, 6H, J ¼ 6.6 Hz, CH(CH3)2); 13C NMR (CDCl3)
d (ppm): 167.18 (C]
O), 150.09 (C]N), 124.20 (SeC]C), 148.42 (C]C), 155.34, 151.12,
133.73, 131.53, 130.32, 129.95, 129.48, 127.14, 126.45, 122.34
(aromatic); TOF MS ESþ m/z: [Mþ] 352 (100%).
1581 (C]C); 1H NMR (CDCl3)
d
(ppm): 7.41 (t, 4H, J ¼ 7.5 Hz, AreH),
7.20 (t, 1H, J ¼ 7.2 Hz, AreH), 7.00 (d, 2H, J ¼ 7.2 Hz, AreH), 6.92 (d,
2H, J ¼ 8.7 Hz, AreH), 7.69 (s, 1H, CH]C), 3.84 (d, 2H, J ¼ 7.8 Hz,
4.3.10. (2Z,5Z)-5-(Benzo[d][1,3]dioxol-4-ylmethylene)-3-isobutyl-
2(phenylimino)thiazolidin-4-one (12)
CH2), 2.37e2.33 (m,1H, CH), 1.01 (d, 6H, J ¼ 6.6 Hz, CH (CH3)2); 13
C
NMR (CDCl3)
d (ppm): 167.36 (C]O), 151.00 (C]N), 124.69 (SeC]
Yield: 85%; m.p:146 ꢁC; Anal. calc. C21H20N2O3S: C 66.30, H 5.30,
N 7.36, S 8.43%. Found: C 66.25, H 5.27, N 7.33, S 8.40%. IR nmax
(cmꢀ1): 1694 (eNeC]O), 1632 (C]N), 756 (CeSeC), 1373 (tert. N),
C), 148.53 (C]C), 133.32, 131.80, 130.55, 129.35, 127.85, 126.53,
122.67, 121.17, 118.85, 114.53 (aromatic), 50.14 (CeN), 26.97 (CH),
20.14 (CH3); TOF MS ESþ m/z: [Mþ] 370 (100%).
1589 (C]C); 1H NMR (CDCl3)
d
(ppm): 7.41 (t, 2H, J ¼ 7.8 Hz, AreH),
7.21 (t, 1H, J ¼ 7.2 Hz, AreH), 7.00 (t, 4H, J ¼ 10.2 Hz, AreH), 6.84 (d,
1H, J ¼ 8.1 Hz, AreH), 7.65 (s, 1H, CH]C), 6.00 (s, 2H, CHO2), 2.17 (d,
2H, J ¼ 6.9 Hz, CH2), 2.39e2.30 (m, 1H, CH), 1.01 (d, 6H, J ¼ 6.6 Hz,
4.3.15. (2Z,5Z)-5-(2,5-Dimethoxybenzylidene)-3-isobutyl-2-
(phenylimino)thiazolidin-4-one (17)
Yield: 85%; m.p: 135 ꢁC; Anal. calc. C22H24N2O3S: C 66.64, H 6.10,
N 7.06, S 8.09%. Found: C 67.09, H 6.01, N 7.10, S 7.95%. IR nmax
(cmꢀ1): 1695 (eNeC]O), 1615 (C]N), 771 (CeSeC), 1372 (tert. N),
CH (CH3)2); 13C NMR (CDCl3)
d(ppm): 167.22 (C]O), 150.70 (C]N),
124.75 (SeC]C), 148.37 (C]C), 148.94, 148.26, 130.57, 129.36,
128.10, 125.86, 121.08, 119.45 (aromatic), 109.05 (CHO2), 50.16
(CeN), 26.94 (CH), 20.11 (CH3); TOF MS ESþ m/z: [Mþ] 380 (100%).
1581 (C]C); 1H NMR (CDCl3)
d (ppm): 7.38e7.33 (m, 2H, AreH),
7.18 (t, 1H, J ¼ 7.2 Hz, AreH), 6.98 (t, 2H, J ¼ 7.2 Hz, AreH), 6.92
(d, 1H, J ¼ 8.4 Hz, AreH), 6.85e6.80 (m, 2H, AreH), 8.08 (s, 1H, CH]
C), 3.84 (s, 6H, (OCH3)2), 3.81 (d, 2H, J ¼ 7.2 Hz, CH2), 2.37e2.32 (m,
4.3.11. (2Z,5Z)-3-Isobutyl-2-(phenylimino)-5-(pyridine-2-ylmethylne)
thiazolidin-4-one (13)
1H, CH),1.01 (d, 6H, J ¼ 6.9 Hz, CH(CH3)2); 13C NMR (CDCl3)
d (ppm):
Yield: 85%; m.p: 196 ꢁC: Anal. calc. C19H19N3OS: C 67.63, H 5.68,
N 12.45, S 9.50%. Found: C 67.97, H 5.65, N 12.57, S 9.27%. IR nmax
(cmꢀ1): 1700 (eNeC]O), 1634 (C]N), 763 (CeSeC), 1342 (tert. N),
167.06 (C]O), 150.88 (C]N), 124.70 (SeC]C), 148.30 (C]C),
153.37, 152.27, 129.30, 125.90, 123.79, 122.18, 121.11, 115.84, 114.60,
111.96 (aromatic), 56.07 (OCH3), 55.80 (OCH3), 50.14 (CeN), 26.98
(CH2), 20.16 (CH3); TOF MS ESþ m/z: [Mþ] 396 (100%).
1577 (C]C); 1H NMR (CDCl3)
d
(ppm): 8.65 (d, 1H, J ¼ 4.5 Hz AreH),
7.72e7.70 (m, 1H, AreH), 7.45e7.38 (m, 3H, AreH), 7.20e7.15 (m,
2H, AreH), 7.03 (t, 2H, J ¼ 8.7 Hz, AreH), 7.73 (s, 1H, CH]C), 3.85 (d,
2H, J ¼ 7.5 Hz, CH2), 2.40e2.31 (m, 1H, CH), 1.01 (d, 6H, J ¼ 6.9 Hz,
4.3.16. (2Z,5Z)-5-(4-Ethylbenzylidene)-3-isobutyl-2-(phenylimino)
thiazolidi-4-one (18)
CH (CH3)2); 13C NMR (CDCl3)
d
(ppm): 1679.22 (C]O), 149.28 (C]
Yield: 85%; m.p: 125 ꢁC; Anal. calc. C22H24N2OS: C 72.49, H 6.64,
N 7.69, S 8.80%. Found: C 72.73, H 6.562, N 7.74, S 8.566%. IR nmax
(cmꢀ1): 1706 (eNeC]O), 1625 (C]N), 759 (CeSeC), 1372 (tert. N),
N), 124.47 (SeC]C), 148.26 (C]C), 154.18, 152.49, 136.65, 129.28,
127.31, 126.51, 126.27, 122.69, 121.22 (aromatic), 9.58 (CeN), 27.02
(CH), 20.13 (CH3); TOF MS ESþ m/z: [Mþ] 337 (100%).
1586 (C]C); 1H NMR (CDCl3)
d
(ppm): 7.41 (t, 4H, J ¼ 7.8 Hz, AreH),
7.25e7.15 (m, 3H, AreH), 7.00 (t, 2H, J ¼ 7.2 Hz, AreH), 7.72 (s, 1H,
CH]C), 3.84 (d, 2H, J ¼ 7.5 Hz, CH2), 2.40e2.31 (m, 1H, CH), 1.01 (d,
6H, J ¼ 6.9 Hz, CH(CH3)2), 2.69 (q, 2H, J ¼ 7.5 Hz, CH2), 1.24 (t, 3H,
4.3.12. (2Z,5Z)-3-isobutyl-5-((3-Methylthiophene-2-yl)methylene-
2-(phenylimino)thiazolidin-4-one (14)
Yield: 85%; m.p: 172 ꢁC; Anal. calc. C19H20N2OS2: C 64.01, H 5.65,
N 7.86, S 17.99%. Found: C 64.00, H 5.63, N 7.84, S 17.95%. IR nmax
J ¼ 7.5 Hz, CH3); 13C NMR (CDCl3)
d (ppm): 167.27 (C]O), 150.94
(C]N), 124.74 (SeC]C), 148.44 (C]C), 146.49, 131.30, 130.84,