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M.D. Altıntop et al. / European Journal of Medicinal Chemistry 58 (2012) 299e307
13C NMR (125 MHz, DMSO-d6): 34.10 (CH3), 36.32 (CH2), 36.37
153.93 (C), 163.55 (C), 168.74 (C). For C11H11FN6OS calculated: C,
44.89; H, 3.77; N, 28.56; found: C, 44.90; H, 3.76; N, 28.57.
MS (FAB) [M þ 1]þ: m/z 295.
(2CH3), 112.21 (2CH), 121.63 (C), 128.70 (2CH), 145.40 (CH), 151.95
(C), 154.08 (C), 167.86 (C). For C13H17N7OS calculated: C, 48.89; H,
5.36; N, 30.70; found: C, 48.90; H, 5.35; N, 30.68.
5.1.1.3.16. N0-(2-Chlorobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (16). 1H NMR (500 MHz, DMSO-d6): 3.99 (3H, s),
4.20 and 4.64 (2H, 2s), 7.43e8.00 (4H, m), 8.43 and 8.59 (1H, 2s),11.93
and 12.05 (1H, 2s).
MS (FAB) [M þ 1]þ: m/z 320.
5.1.1.3.9. N0-(4-(Trifluoromethyl)benzylidene)-2-[(1-methyl-1H-
tetrazol-5-yl)thio]acetohydrazide (9). 1H NMR (500 MHz, DMSO-
d6): 3.99 (3H, s), 4.22 and 4.65 (2H, 2s), 7.82 (2H, d, J ¼ 8.5 Hz), 7.93
(2H, d, J ¼ 8 Hz), 8.11 and 8.27 (1H, 2s), 11.96 (1H, s).
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.15 (CH2), 124.10
(C), 126.19 (2CH), 128.02 (2CH), 133.30 (C), 137.00 (C), 142.94 (CH),
153.91 (C), 168.82 (C). For C12H11F3N6OS calculated: C, 41.86; H,
3.22; N, 24.41; found: C, 41.85; H, 3.20; N, 24.43.
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.17 (CH2), 127.36
(CH), 128.13 (CH), 130.42 (CH), 131.60 (CH), 131.99 (C), 133.51 (C),
140.61 (CH), 153.93 (C), 168.72 (C). For C11H11ClN6OS calculated: C,
42.51; H, 3.57; N, 27.04; found: C, 42.50; H, 3.59; N, 27.03.
MS (FAB) [M þ 1]þ: m/z 311.
5.1.1.3.17. N0-(3-Chlorobenzylidene)-2-[(1-methyl-1H-tetrazol-5-
yl)thio]acetohydrazide (17). 1H NMR (500 MHz, DMSO-d6): 3.99
(3H, s), 4.20 and 4.63 (2H, 2s), 7.46e7.79 (4H, m), 8.02 and 8.17 (1H,
2s), 11.86 and 11.96 (1H, 2s).
MS (FAB) [M þ 1]þ: m/z 345.
5.1.1.3.10. N0-(4-Hydroxybenzylidene)-2-[(1-methyl-1H-tetrazol-
5-yl)thio]acetohydrazide (10). 1H NMR (500 MHz, DMSO-d6): 3.99
(3H, s), 4.16 and 4.58 (2H, 2s), 6.82 (2H, s), 7.52 (2H, s), 7.93 and 8.07
(1H, 2s), 9.96 (1H, s), 11.57 and 11.60 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.13 (CH3), 36.12 (CH2), 126.24
(CH), 126.62 (CH), 130.19 (CH), 131.22 (CH), 134.15 (C), 136.57 (C),
142.98 (CH), 153.93 (C), 168.72 (C). For C11H11ClN6OS calculated: C,
42.51; H, 3.57; N, 27.04; found: C, 42.51; H, 3.58; N, 27.03.
MS (FAB) [M þ 1]þ: m/z 311.
13C NMR (125 MHz, DMSO-d6): 34.11 (CH3), 36.32 (CH2), 116.17
(2CH), 125.33 (C), 129.14 (2CH), 144.89 (CH), 154.02 (C), 159.85 (C),
168.12 (C). For C11H12N6O2S calculated: C, 45.20; H, 4.14; N, 28.75;
found: C, 45.19; H, 4.15; N, 28.76.
5.1.1.3.18. N0-(2-Bromobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (18). 1H NMR (500 MHz, DMSO-d6): 3.99 (3H, s),
4.20 and 4.64 (2H, 2s), 7.39e7.97 (4H, m), 8.39 and 8.54 (1H, 2s),11.96
and 12.08 (1H, 2s).
MS (FAB) [M þ 1]þ: m/z 293.
5.1.1.3.11. N0-(4-Methoxybenzylidene)-2-[(1-methyl-1H-tetra-
zol-5-yl)thio]acetohydrazide (11). 1H NMR (500 MHz, DMSO-d6):
3.81 (3H, s), 3.99 (3H, s), 4.17 and 4.60 (2H, 2s), 7.02 (2H, d,
J ¼ 8.5 Hz), 7.65 (2H, d, J ¼ 9 Hz), 7.98 and 8.13 (1H, 2s), 11.64 and
11.68 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.19 (CH2), 123.84
(C), 127.74 (CH), 128.62 (CH), 132.23 (CH), 133.09 (CH), 133.65 (C),
142.96 (CH), 153.90 (C), 168.71 (C). For C11H11BrN6OS calculated: C,
37.19; H, 3.12; N, 23.66; found: C, 37.20; H, 3.11; N, 23.65.
MS (FAB) [M þ 1]þ: m/z 356.
13C NMR (125 MHz, DMSO-d6): 34.11 (CH3), 36.29 (CH2), 55.78
(CH3), 114.81 (2CH), 126.91 (C), 129.01 (2CH), 144.46 (CH), 154.01
(C), 161.27 (C), 168.25 (C). For C12H14N6O2S calculated: C, 47.05; H,
4.61; N, 27.43; found: C, 47.06; H, 4.59; N, 27.44.
5.1.1.3.19. N0-(3-Bromobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (19). 1H NMR (500 MHz, DMSO-d6): 3.99 (3H, s),
4.20 and 4.64 (2H, 2s), 7.41e7.93 (4H, m), 8.01 and 8.17 (1H, 2s), 11.86
and 11.93 (1H, 2s).
MS (FAB) [M þ 1]þ: m/z 307.
5.1.1.3.12. N0-(2-Nitrobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (12). 1H NMR (500 MHz, DMSO-d6): 3.99 (3H, s),
4.21 and 4.62 (2H, 2s), 7.67e8.11 (4H, m), 8.43 and 8.60 (1H, 2s),
12.03 and 12.16 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.15 (CH2), 122.69
(C), 126.59 (CH), 129.54 (CH), 131.46 (CH), 133.07 (CH), 136.81 (C),
142.89 (CH), 153.93 (C), 168.72 (C). For C11H11BrN6OS calculated: C,
37.19; H, 3.12; N, 23.66; found: C, 37.18; H, 3.10; N, 23.67.
MS (FAB) [M þ 1]þ: m/z 356.
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.11 (CH2), 125.10
(CH), 128.73 (C), 131.16 (CH), 131.30 (CH), 134.14 (CH), 143.54 (CH),
148.54 (C), 154.01 (C), 168.85 (C). C11H11N7O3S calculated: C, 41.12;
H, 3.45; N, 30.51; found: C, 41.10; H, 3.45; N, 30.49.
MS (FAB) [M þ 1]þ: m/z 322.
5.1.1.3.20. N0-(2-Hydroxybenzylidene)-2-[(1-methyl-1H-tetrazol-
5-yl)thio]acetohydrazide (20). 1H NMR (500 MHz, DMSO-d6): 3.99
(3H, s), 4.20 and 4.61 (2H, 2s), 6.86e7.71 (4H, m), 8.34 and 8.42 (1H,
2s), 10.08 and 10.91 (1H, 2s), 11.69 and 12.00 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.11 (CH3), 36.36 (CH2), 116.82
(CH), 119.09 (C), 120.45 (CH), 126.67 (CH), 132.05 (CH), 141.94 (CH),
153.99 (C), 156.92 (C), 168.19 (C). For C11H12N6O2S calculated: C,
45.20; H, 4.14; N, 28.75; found: C, 45.21; H, 4.13; N, 28.74.
MS (FAB) [M þ 1]þ: m/z 293.
5.1.1.3.13. N0-(3-Nitrobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (13). 1H NMR (500 MHz, DMSO-d6): 4.00 (3H, s),
4.23 and 4.67 (2H, 2s), 7.74e8.55 (5H, m), 11.99 and 12.07 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.13 (CH2), 121.68
(CH), 124.77 (CH), 130.92 (CH), 133.46 (CH), 136.20 (C), 142.39 (CH),
148.73 (C), 153.92 (C), 168.83 (C). For C11H11N7O3S calculated: C,
41.12; H, 3.45; N, 30.51; found: C, 41.12; H, 3.44; N, 30.52.
MS (FAB) [M þ 1]þ: m/z 322.
5.1.1.3.21. N0-(3-Hydroxybenzylidene)-2-[(1-methyl-1H-tetrazol-
5-yl)thio]acetohydrazide (21). 1H NMR (500 MHz, DMSO-d6): 3.99
(3H, s), 4.18 and 4.62 (2H, 2s), 6.83e7.27 (4H, m), 7.95 and 8.10 (1H,
2s), 9.64 and 9.67 (1H, 2s), 11.71 and 11.75 (1H, 2s).
5.1.1.3.14. N0-(2-Fluorobenzylidene)-2-[(1-methyl-1H-tetrazol-5-
yl)thio]acetohydrazide (14). 1H NMR (500 MHz, DMSO-d6): 3.99
(3H, s), 4.19 and 4.63 (2H, 2s), 7.25e7.94 (4H, m), 8.24 and 8.41 (1H,
2s), 11.88 and 11.96 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.11 (CH3), 36.36 (CH2), 113.03
(CH), 117.91 (CH), 119.05 (CH), 130.38 (CH), 135.55 (C), 144.84 (CH),
154.00 (C), 158.12 (C), 168.41 (C). For C11H12N6O2S calculated: C,
45.20; H, 4.14; N, 28.75; found: C, 45.20; H, 4.12; N, 28.77.
MS (FAB) [Mþ1]þ: m/z 293.
13C NMR (125 MHz, DMSO-d6): 34.13 (CH3), 36.11 (CH2), 116.44
(CH), 121.84 (C), 125.45 (CH), 132.47 (CH), 137.43 (CH), 142.39 (CH),
153.92 (C), 160.16 (C), 168.65 (C). For C11H11FN6OS calculated: C,
44.89; H, 3.77; N, 28.56; found: C, 44.88; H, 3.76; N, 28.56.
MS (FAB) [M þ 1]þ: m/z 295.
5.1.1.3.22. N0-(2-Methoxybenzylidene)-2-[(1-methyl-1H-tetrazol-
5-yl)thio]acetohydrazide (22). 1H NMR (500 MHz, DMSO-d6): 3.86
(3H, s), 3.99 (3H, s), 4.16 and 4.61 (2H, 2s), 7.00e7.83 (4H, m), 8.37
and 8.53 (1H, 2s), 11.72 and 11.80 (1H, 2s).
5.1.1.3.15. N0-(3-Fluorobenzylidene)-2-[(1-methyl-1H-tetrazol-5-yl)
thio]acetohydrazide (15). 1H NMR (500 MHz, DMSO-d6): 3.99 (3H, s),
4.20 and 4.63 (2H, 2s), 7.27e7.57 (4H, m), 8.03 and 8.20 (1H, 2s),11.86
and 11.93 (1H, 2s).
13C NMR (125 MHz, DMSO-d6): 34.12 (CH3), 36.31 (CH2), 56.18
(CH3), 112.33 (CH), 121.21 (C), 125.90 (CH), 132.07 (2CH), 140.23
(CH), 153.98 (C), 158.15 (C), 168.40 (C). For C12H14N6O2S calculated:
C, 47.05; H, 4.61; N, 27.43; found: C, 47.05; H, 4.60; N, 27.45.
13C NMR (125 MHz, DMSO-d6): 34.14 (CH3), 36.11 (CH2), 113.28
(CH), 117.36 (CH), 123.91 (CH), 131.36 (CH), 136.89 (C), 143.16 (CH),