M. D'Ascenzio et al. / European Journal of Medicinal Chemistry 86 (2014) 17e30
27
4.61. 3-Benzyl-2-(2-(thiophen-2-ylmethylene)hydrazono)
thiazolidin-4-one (24B)
8.16e8.19 (m, 1H, pyridine), 8.62e8.63 (m, 1H, pyridine), 8.99e9.00
(m, 1H, pyridine). 13C NMR (101 MHz, DMSO-d6):
15.01, 32.62,
d
46.45, 124.02, 128.06, 128.42, 128.90, 134.00, 134.23, 136.54, 150.72,
160.63, 163.98, 172.77 (one carbon missing due to overlapping
signals). Anal. Calcd. for C17H16N4OS: C, 62.94; H, 4.97; N, 17.27.
Found: C, 63.26; H, 5.21; N, 17.60.
White powder, mp 99e101 ꢂC, 89% yield; 1H NMR (400 MHz,
CDCl3): d 3.84 (s, 2H, CH2-thiaz.), 5.01 (s, 2H, CH2-benzyl), 7.08e7.11
(m, 1H, thiophene), 7.28e7.37 (m, 4H, Ar), 7.43e7.44 (m, 1H, Ar),
7.50e7.51 (m, 2H, thiophene), 8.57 (s, 1H, CH]). 13C NMR (101 MHz,
DMSO-d6):
132.92, 136.37, 139.07, 152.64, 163.87, 172.73. Anal. Calcd. for
15H13N3OS2: C, 57.12; H, 4.15; N, 13.32. Found: C, 57.44; H, 4.39; N,
d
32.56, 46.14, 127.99, 128.08, 128.55, 128.92, 130.60,
4.67. 3-Benzyl-2-(2-(pyridin-4-ylmethylene)hydrazono)
thiazolidin-4-one (30B)
C
13.60.
Green powder, mp 190e192 ꢂC, 75% yield; 1H NMR (400 MHz,
DMSO-d6):
d 4.09 (s, 2H, CH2-thiaz.), 4.92 (s, 2H, CH2-benzyl),
4.62. 3-Benzyl-2-(2-(1-(thiophen-2-yl)ethylidene)hydrazono)
thiazolidin-4-one (25B)
7.27e7.37 (m, 5H, Ar), 7.67e7.69 (m, 2H, pyridine), 8.49 (s, 1H,
CH]), 8.66e8.67 (m, 2H, pyridine). 13C NMR (101 MHz, DMSO-d6):
d
32.69, 46.28, 121.86, 128.04, 128.95, 136.22, 141.62, 145.21, 150.79,
Light orange powder, mp 105e107 ꢂC, 77% yield; 1H NMR
156.43,167.02,172.89. Anal. Calcd. for C16H14N4OS: C, 61.92; H, 4.55;
N, 18.05. Found: C, 61.67; H, 4.22; N, 17.79.
(400 MHz, DMSO-d6):
d 2.35 (s, 3H, CH3), 4.03 (s, 2H, CH2-thiaz.),
4.91 (s, 2H, CH2-benzyl), 7.10e7.13 (m,1H, thiophene), 7.14e7.41 (m,
5H, Ar), 7.51e7.53 (m, 1H, thiophene), 7.61e7.62 (m, 1H, thiophene).
4.68. 3-Benzyl-2-(2-(1-(pyridin-4-yl)ethylidene)hydrazono)
thiazolidin-4-one (31B)
13C NMR (101 MHz, DMSO-d6):
d
15.36, 32.57, 46.39, 128.03, 128.20,
128.44, 128.86, 129.20, 129.97, 136.57, 143.43, 158.14, 162.36, 172.70.
Anal. Calcd. for C16H15N3OS2: C, 58.33; H, 4.59; N, 12.76. Found: C,
58.04; H, 4.78; N, 12.48.
Green powder, mp 137e139 ꢂC, 96% yield; 1H NMR (400 MHz,
DMSO-d6):
CH2-benzyl), 7.28e7.39 (m, 5H, Ar), 7.72e7.73 (m, 2H, pyridine),
8.63e8.64 (m, 2H, pyridine). 13C NMR (101 MHz, DMSO-d6):
14.77,
d 2.34 (s, 3H, CH3), 4.07 (s, 2H, CH2-thiaz.), 4.93 (s, 2H,
4.63. 3-Benzyl-2-(2-(1-phenylethylidene)hydrazono)thiazolidin-4-
d
one (26B)
32.67, 46.51, 120.96, 128.07, 128.42, 128.90, 136.46, 144.93, 150.53,
160.81, 165.01, 172.77. Anal. Calcd. for C17H16N4OS: C, 62.94; H, 4.97;
N, 17.27. Found: C, 62.77; H, 4.75; N, 17.03.
Orange powder, mp 93e95 ꢂC, 76%yield; 1H NMR (400 MHz,
DMSO-d6):
CH2-benzyl), 7.28e7.39 (m, 6H, Ar), 7.42e7.44 (m, 2H, Ar),
7.81e7.83 (m, 2H, Ar); 13C NMR (101 MHz, DMSO-d6):
15.18, 32.54,
d 2.35 (s, 3H, CH3), 4.04 (s, 2H, CH2-thiaz.), 4.93 (s, 2H,
4.69. 2-(2-((1H-Indol-3-yl)methylene)hydrazono)-3-
benzylthiazolidin-4-one (32B)
d
46.44, 126.93, 128.04, 128.42, 128.88, 130.42, 136.60, 138.06, 139.51,
162.38, 162.91, 172.72. Anal. Calcd. for C18H17N3OS: C, 66.85; H,
5.30; N, 12.99. Found: C, 66.53; H, 5.57; N, 13.31.
Yellow powder, mp 238e240 ꢂC, 90% yield; 1H NMR (400 MHz,
DMSO-d6):
7.13e7.83 (m, 10H, indole þ Ar), 8.58 (s, 1H, CH]), 11.68 (bs, 1H, NH,
D2O exch.). 13C NMR (101 MHz, DMSO-d6):
32.45, 46.12, 112.31,
d 4.01 (s, 2H, CH2-thiaz.), 4.91 (s, 2H, CH2-benzyl),
4.64. 3-Benzyl-2-(2-(1-(pyridin-2-yl)ethylidene)hydrazono)
d
thiazolidin-4-one (27B)
112.47, 121.28, 122.48, 123.21, 124.98, 127.94, 128.12, 128.94, 132.62,
133.64, 140.96, 154.35, 160.70, 172.72. Anal. Calcd. for C19H16N4OS:
C, 65.50; H, 4.63; N, 16.08. Found: C, 65.34; H, 4.46; N, 15.80.
White powder, mp 163e165 ꢂC, 89% yield; 1H NMR (400 MHz,
DMSO-d6):
d 2.39 (s, 3H, CH3), 4.06 (s, 2H, CH2-thiaz.), 4.93 (s, 2H,
CH2-benzyl), 7.27e7.39 (m, 5H, Ar), 7.41e7.44 (m, 1H, pyridine),
7.83e7.87 (m, 1H, pyridine), 8.03e8.05 (m, 1H, pyridine), 8.60e8.61
4.70. 2-(2-(Benzo[d][1,3]dioxol-5-ylmethylene)hydrazono)-3-
benzylthiazolidin-4-one (33B)
(m, 1H, pyridine). 13C NMR (101 MHz, DMSO-d6):
d 14.09, 32.63,
46.50, 120.93, 125.09, 128.08, 128.49, 128.89, 136.50, 137.26, 149.32,
152.65, 163.17, 164.46, 172.79. Anal. Calcd. for C17H16N4OS: C, 62.94;
H, 4.97; N, 17.27. Found: C, 63.21; H, 5.18; N, 17.54.
Light yellow powder, mp 153e155 ꢂC, 78% yield; 1H NMR
(400 MHz, CDCl3):
d 3.80 (s, 2H, CH2-thiaz.), 5.05 (s, 2H, CH2-
benzyl), 6.04 (s, 2H, OCH2O), 6.84 (d, 1H, J ¼ 7.8 Hz, benzodioxole),
7.14 (d, 1H, J ¼ 7.8 Hz, benzodioxole), 7.31e7.34 (m, 3H, Ar), 7.41 (s,
1H, benzodioxole), 7.49e7.51 (m, 2H, Ar), 8.40 (s, 1H, CH]). 13C
4.65. 3-Benzyl-2-(2-(pyridin-3-ylmethylene)hydrazono)
thiazolidin-4-one (28B)
NMR (101 MHz, DMSO-d6): d 32.65, 45.77, 106.17, 108.57, 124.72,
128.01, 128.87, 128.92, 135.92, 148.35, 150.19, 157.41, 161.87, 163.83,
171.09, 172.76. Anal. Calcd. for C18H15N3O3S: C, 61.18; H, 4.28; N,
11.89. Found: C, 61.05; H, 4.07; N, 12.08.
Dark brown powder, mp 117e119 ꢂC, 71% yield; 1H NMR
(400 MHz, DMSO-d6):
d 4.09 (s, 2H, CH2-thiaz.), 4.92 (s, 2H, CH2-
benzyl), 7.27e7.36 (m, 5H, Ar), 7.48e7.51 (m, 1H, pyridine),
8.14e8.16 (m, 1H, pyridine), 8.54 (s, 1H, CH]), 8.63e8.64 (m, 1H,
pyridine), 8.91 (s, 1H, pyridine). 13C NMR (101 MHz, DMSO-d6):
4.71. 2-(2-((Naphthalen-1-yl)methylene)hydrazono)-3-
benzylthiazolidin-4-one (34B)
d
32.54, 46.44, 121.85, 124.52, 128.11, 128.48, 128.82, 130.59, 136.43,
138.19,139.98,163.88,165.47,172.62. Anal. Calcd. for C16H14N4OS: C,
61.92; H, 4.55; N, 18.05. Found: C, 62.20; H, 4.84; N, 18.24.
Yellow powder, mp 137e139 ꢂC, 83% yield; 1H NMR (400 MHz,
CDCl3): d 3.85 (s, 2H, CH2-thiaz.), 5.09 (s, 2H, CH2-benzyl), 7.31e7.38
(m, 3H, Ar), 7.52e7.58 (m, 4H, Ar), 7.61e7.66 (m, 1H, Ar), 7.90e7.97
4.66. 3-Benzyl-2-(2-(1-(pyridin-3-yl)ethylidene)hydrazono)
(m, 3H, Ar), 8.93e8.95 (m, 1H, Ar), 9.10 (s, 1H, CH]). 13C NMR
thiazolidin-4-one (29B)
(101 MHz, DMSO-d6): d 32.71, 46.28, 125.98, 126.84, 128.08, 128.97,
129.28, 129.79, 131.07, 131.94, 134.06, 136.37, 159.32, 163.91, 165.19,
173.09 (three carbons missing due to overlapping signals). Anal.
Calcd. for C21H17N3OS: C, 70.17; H, 4.77; N, 11.69. Found: C, 69.98; H,
4.34; N, 12.90.
Brown powder, mp 148e150 ꢂC, 99% yield; 1H NMR (400 MHz,
DMSO-d6):
d 2.39 (s, 3H, CH3), 4.07 (s, 2H, CH2-thiaz.), 4.95 (s, 2H,
CH2-benzyl), 7.30e7.41 (m, 5H, Ar), 7.46e7.49 (m, 1H, pyridine),