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H 6.09, N 35.13; found: C 47.39, H 5.97, N 35.35%; IR:
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)
νmax (cm−1) 3347 (NH), 1576 (C N), 1285 (C N), 1038
cyclopentyl thiosemicarbazide (9): light brown solid. Yield:
53%; mp: 132 ◦C. Anal. calc. for C12H17N7S: C 49.46, H
5.88, N 33.65; found: C 49.39, H 5.94, N 33.85%; IR: νmax
(cm−1) 3310 (NH), 1541 (C N), 1309 (C N), 1014 (C S),
968 (N N); 1H NMR (CDCl3): (δ, ppm) 2.82–2.93 (8H, m,
CH2), 3.01 (3H, s, CH3 C N), 3.06 (3H, s, CH3 C N),
4.01–4.20 (1H, m, N CH), 7.86 (1H, d, NH), 8.69 (1H,
s, NH); 13C NMR (CDCl3): (δ, ppm) 188.0 (C S), 164.0
(C N), 163.8 (C N), 163.01 (C N), 162.4 (C N), 56.4
(CH N), 32.6 (2 CH2), 22.4 (2 CH2), 15.4 (CH3), 13.1
(CH3).
1
(C S), 942 (N N); H NMR (CDCl3): (δ, ppm) 1.94–1.21
(6H, m, CH2 CH3), 3.04 (3H, s, CH3 C N), 3.08 (3H,
s, CH3 C N), 4.17 (4H, s, CH2 N CH2), 8.94 (1H, s,
NH); 13C NMR (CDCl3): (δ, ppm) 189.4 (C S), 164.7
(C N), 163.4 (C N), 163.1 (C N), 162.6 (C N), 56.5 (2
CH2 N), 15.1 (CH3), 13.7 (CH3), 13.1 (2 CH3).
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)-
n-butylamine thiosemicarbazide (5): white solid. Yield:
39%; mp: 145 ◦C. Anal. calc. for C11H17N7S: C 47.29, H
6.13, N 35.10; found: C 47.42, H 6.28, N 35.26%; IR: νmax
(cm−1) 3411 (NH), 1559 (C N), 1289 (C N), 1062 (C S),
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)
cyclohexyl thiosemicarbazide (10): white solid. Yield: 51%;
mp: 117 ◦C. Anal. calc. for C13H19N7S: C 51.13, H 6.27, N
1
965 (N N); H NMR (CDCl3): (δ, ppm) 1.92–1.99 (3H,
m, CH2 CH3), 2.42–2.59 (4H, m, CH2), 3.06 (3H, s,
CH3 C N), 3.11 (3H, s, CH3 C N), 3.90–4.01 (2H, m,
NH CH2), 8.21 (1H, t, NH), 8.89 (1H, s, NH); 13C
NMR (CDCl3): (δ, ppm) 186.8 (C S), 164.0 (C N), 163.8
(C N), 163.5 (C N), 163.0 (C N), 50.5 (CH2 N), 35.3
(CH2), 21.8 (CH2), 14.8 (CH3), 13.6 (CH3), 13.4 (CH3).
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)-
isobutylamine thiosemicarbazide (6): white solid. Yield:
48%; mp: 182 ◦C. Anal. calc. for C11H17N7S: C 47.29,
H 6.13, N 35.10; found: C 47.48, H 6.33, N 35.21%; IR:
νmax (cm−1) 3426 (NH), 1596 (C N), 1307 (C N), 1035
32.10; found: C 51.05, H 6.24, N 31.96%; IR: νmax (cm−1
)
3221 (NH), 1526 (C N), 1299 (C N), 1026 (C S), 971
1
(N N); H NMR (CDCl3): (δ, ppm) 2.29–2.50 (10H, m,
CH2); 3.03 (3H, s, CH3 C N), 3.08 (3H, s, CH3 C N),
4.03 (1H, s, N CH), 8.02 (1H, d, NH), 8.91 (1H, s, NH);
13C NMR (CDCl3): (δ, ppm) 187.3 (C S), 164.0 (C N),
163.2 (C N), 163.0 (C N), 162.8 (C N), 54.2 (CH N),
35.6 (2 CH2), 29.5 (CH2), 25.4 (2 CH2), 15.3 (CH3), 13.9
(CH3).
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)
cyclooctyl thiosemicarbazide (11): white solid. Yield: 39%;
mp: 158 ◦C. Anal. calc. for C15H23N7S: C 54.03, H 6.95, N
1
(C S), 968 (N N); H NMR (CDCl3): (δ, ppm) 2.01–2.15
(6H, m, CH CH3), 2.59–2.69 (1H, m, CH), 3.06 (3H, s,
CH3 C N), 3.10 (3H, s, CH3 C N), 4.15 (2H, d, N CH2),
8.35 (1H, d, NH), 9.14 (1H, s, NH); 13C NMR (CDCl3):
(δ, ppm) 187.4 (C S), 164.1 (C N), 163.9 (C N), 163.5
(C N), 163.1 (C N), 54.9 (CH N), 32.6 (CH2), 22.4 (CH3),
14.9 (CH3), 13.3 (CH3), 10.2 (CH3).
29.40; found: C 54.05, H 7.04, N 29.56%; IR: νmax (cm−1
)
3256 (NH), 1542 (C N), 1343 (C N), 1058 (C S), 978
1
(N N); H NMR (CDCl3): (δ, ppm) 2.51–2.83 (14H, m,
CH2), 3.01 (3H, s, CH3 C N), 3.04 (3H, s, CH3 C N),
4.59–4.61 (1H, m, N CH), 8.13 (1H, d, NH), 9.03 (1H,
s, NH); 13C NMR (CDCl3): (δ, ppm) 186.8 (C S), 163.9
(C N), 163.5 (C N), 163.2 (C N), 162.8 (C N), 55.8
(CH N), 38.1 (2 CH2), 29.5 (3 CH2), 26.4 (2 CH2), 14.8
(CH3), 13.4 (CH3).
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)-
n-methylbutyl thiosemicarbazide (7): light yellow solid.
Yield: 43%; mp: 162 ◦C. Anal. calc. for C12H19N7S: C
49.13, H 6.53, N 33.42; found: C 49.29, H 6.24, N 33.53%;
IR: νmax (cm−1) 3426 (NH), 1595 (C N), 1309 (C N),
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)
hexamethyleneimine thiosemicarbazide (12): light yellow
solid. Yield: 47%; mp: 135 ◦C. Anal. calc. for C13H19N7S: C
51.13, H 6.27, N 32.10; found: C 51.05, H 6.24, N 32.02%;
IR: νmax (cm−1) 3315 (NH), 1540 (C N), 1298 (C N), 1054
1
1038 (C S), 968 (N N); H NMR (CDCl3): (δ, ppm) 1.79
(3H, t, CH2 CH3), 2.39–2.48 (4H, m, CH2), 3.04 (3H, s,
CH3 C N), 3.10 (3H, s, CH3 C N), 2.65 (3H, s, N CH3),
3.99 (2H, t, N CH2), 9.23 (1H, s, NH); 13C NMR (CDCl3):
(δ, ppm) 187.3 (C S), 163.8 (C N), 163.6 (C N), 163.4
(C N), 163.0 (C N), 57.6 (CH2 N), 40.4 (CH3 N), 32.6
(CH2), 22.6 (CH2), 15.6 (CH3), 13.6 (CH3), 13.3 (CH3).
3(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)-
dipropylamine thiosemicarbazide (8): white solid. Yield:
47%; mp: 158 ◦C. Anal. calc. for C13H21N7S: C 50.79,
H 6.89, N 31.89; found: C 51.05, H 6.99, N 31.63%; IR:
νmax (cm−1) 3426 (NH), 1541 (C N), 1303 (C N), 1077
1
(C S), 971 (N N); H NMR (CDCl3): (δ, ppm) 2.82–2.97
(8H, m, CH2), 3.02 (3H, s, CH3 C N), 3.06 (3H, s,
CH3 C N), 4.54–4.59 (4H, m, CH2 N CH2 ), 7.97 (1H,
s, NH); 13C NMR (CDCl3): (δ, ppm) 187.1 (C S), 163.7
(C N), 163.6 (C N), 163.1 (C N), 162.8 (C N), 55.3 (2
CH2 N), 30.5 (2 CH2), 27.4 (2 CH2), 15.2 (CH3), 13.3
(CH3).
3-(3,7-Dimethyl-4H-pyrazolo[3,4-e][1,2,4]triazin-4-yl)-
4-methylpiperidine thiosemicarbazide (13): light brown
solid. Yield: 50%; mp: 148 ◦C. Anal. calc. for C13H19N7S: C
51.13, H 6.27, N 32.10; found: C 51.15, H 6.39, N 31.97%;
IR: νmax (cm−1) 3125 (NH), 1545 (C N), 1297 (C N),
1
(C S), 968 (N N); H NMR (CDCl3): (δ, ppm) 1.90–2.01
(6H, m, CH2 CH3), 2.58–2.60 (4H, m, CH2), 3.04
(3H, s, CH3 C N), 3.07 (3H, s, CH3 C N), 4.21 (4H, s,
CH2 N CH2), 9.20 (1H, s, NH); 13C NMR (CDCl3):
(δ, ppm) 187.1 (C S), 164.3 (C N), 163.9 (C N), 163.6
(C N), 162.9 (C N), 57.9 (2 CH2 N), 23.5 (2 CH2), 14.7
(CH3), 13.1 (CH3), 13.0 (2 CH3).
1
1088 (C S), 966 (N N); H NMR (CDCl3): (δ, ppm) 1.99
(3H, s, CH3), 2.44–2.63 (4H, m, CH(CH2)2), 3.01 (3H,
s, CH3 C N), 3.06 (3H, s, CH3 C N), 3.60–3.69 (1H,