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M. C. Sarva et al. / Bioorg. Med. Chem. 10 (2002) 313–323
321
3277, 3059, 2930, 2816, 1635, 1500, 1450, 1238, 1026,
1
3299, 3164, 2931, 2817, 1611, 1497, 1444, 1335, 1238,
1028, 750 (cmꢀ1); 1H NMR (DMSO-d6) d 7.98–7.85 (m,
2H), 7.42–7.30 (m, 2H), 7.00–6.78 (m, 4H), 5.8531 (br s,
2H), 4.23 (t, J=6.8, 2H), 3.76 (s, 3H), 3.08–2.78 (m,
4H), 2.68–2.24 (m+s, 6H+3H), 2.10–1.85 (m, 2H).
744 (cmꢀ1); H NMR (DMSO-d6) d 7.72–7.45 (m, 4H),
7.00–6.78 (m, 4H), 5.6431 (br s, 2H), 4.24 (t, J=7.0, 2H),
3.76 (s, 3H), 3.10–2.85 (m, 4H), 2.65–2.35 (m, 6H),
2.10–1.87 (m, 2H).
4-Amino-5-(2-chlorophenyl)-2-[3-[4-(2-nitrophenyl)-1-pi-
perazinyl]propyl]-2,4-dihydro-3H[1,2,4]triazole-3-thione
(12d). Flash chromatography purification gave 0.16 g
(17%) of 12d as a yellow solid: mp 126 ꢃC; IR (KBr)
3263, 3069, 2930, 2819, 1641, 1601, 1519, 1448, 1336,
4-Amino-5-(4-methylphenyl)-2-[3-[4-(2-nitrophenyl)-1-pi-
perazinyl]propyl]-2,4-dihydro-3H[1,2,4]triazole-3-thione
(12j). Flash chromatography purification gave 0.17 g
(19%) of 12j as a yellow solid: mp 128 ꢃC; IR (KBr)
3294, 3070, 2928, 2827, 1604, 1513, 1457, 1341, 1231,
1125, 746 (cmꢀ1); 1H NMR (DMSO-d6) d 8.06–7.90 (m,
2H), 7.86–7.70 (m, 1H), 7.64–7.46 (m, 1H), 7.43–7.22
(m, 3H), 7.18–7.03 (m, 1H), 5.8631 (br s, 2H), 4.23 (t,
J=6.8, 2H), 3.10–2.85 (m, 4H), 2.65–2.30 (m+s,
6H+3H), 2.10–1.85 (m, 2H).
1
1220, 1034, 769 (cmꢀ1); H NMR (DMSO-d6) d 7.88–
7.78 (m, 1H), 7.75–7.45 (m, 5H), 7.42–7.25 (m, 1H) 7.20–
7.03 (m, 1H), 5.6531 (br s, 2H), 4.24 (t, J=6.8, 2H), 2.79–
3.18 (m, 4H), 2.70–2.30 (m, 6H), 2.18–1.87 (m, 2H).
4-Amino-2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-
5-(4-methoxyphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-
thione (12e). Flash chromatography purification gave
0.11 g (12%) of 12e as a white solid: mp 98 ꢃC; IR (KBr)
3280, 2933, 2815, 1611, 1499, 1453, 1243, 1022, 833, 744
(cmꢀ1); 1H NMR (DMSO-d6) d 8.10–7.95 (m, 2H),
7.18–7.03 (m, 2H), 7.01–6.78 (m, 4H), 5.8531 (br s, 2H),
4.22 (t, J=7.0, 2H), 3.83 (s, 3H), 3.76 (s, 3H), 3.08–2.75
(m, 4H), 2.72–2.32 (m, 6H), 2.10–1.85 (m, 2H).
4-Amino-5-(4-chlorophenyl)-2-[3-[4-(2-methoxyphenyl)-1-pi-
perazinyl]propyl] - 2,4- dihydro - 3H[1,2,4]triazole- 3 - thione
(12k). Flash chromatography purification gave 0.15 g
(16%) of 12k as a white solid: mp 106 ꢃC; IR (KBr):
3244, 3132, 2943, 2818, 1592, 1494, 1448, 1242, 1093,
1030, 746 (cmꢀ1); 1H NMR (DMSO-d6) d 8.16–8.00 (m,
2H), 7.70–7.56 (m, 2H), 7.00–6.78 (m, 4H), 5.8931 (br s,
2H), 4.24 (t, J=7.0, 2H), 3.76 (s, 3H), 3.05–2.80 (m,
4H), 2.65–2.30 (m, 6H), 2.10–1.87 (m, 2H).
4-Amino-5-(4-methoxyphenyl)-2-[3-[4-(2-nitrophenyl)-1-
piperazinyl]propyl]-2,4-dihydro-3H[1,2,4]triazole-3-thione
(12f). Flash chromatography purification gave 0.17 g
(18%) of 12f as a yellow solid: mp 112 ꢃC; IR (KBr):
3277, 2934, 2826, 1583, 1498, 1458, 1231, 1025, 751
(cmꢀ1); 1H NMR (DMSO-d6) d 8.07–7.90 (m, 2H),
7.85–7.73 (m, 1H), 7.64–7.48 (m, 1H), 7.36–7.22 (m,
1H), 7.18–6.98 (m, 3H), 5.8631 (br s, 2H), 4.22 (t, J=6.8,
2H), 3.83 (s, 3H), 3.76 (s, 3H), 3.12–2.89 (m, 4H), 2.65–
2.30 (m, 6H), 2.10–1.85 (m, 2H).
4-Amino-5-(4-chlorophenyl)-2-[3-[4-(2-nitrophenyl)-1-pi-
perazinyl]propyl]-2,4-dihyro-3H[1,2,4]triazole-3-thione
(12l). Flash chromatography purification gave 0.16 g
(17%) of 12l as a yellow solid: mp 112–114 ꢃC; IR (KBr)
3310, 2945, 2824, 1604, 1516, 1454, 1347, 1233, 1092,
1
838, 748 (cmꢀ1); H NMR (DMSO-d6) d 8.24–7.95 (m,
2H), 7.88–7.75 (m, 1H), 7.72–7.45 (m, 3H), 7.38–7.22
(m, 1H), 7.20–7.03 (m, 1H), 5.9031 (br s, 2H), 4.25 (t,
J=6.8, 2H), 3.15–2.78 (m, 4H), 2.67–2.28 (m, 6H),
2.13–1.83 (m, 2H).
4-Amino-2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-
5-(3-methoxyphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-
thione (12g). Flash chromatography purification gave
0.16 g (18%) of 12g as a white solid: mp 145 ꢃC; IR
(KBr): 3265, 3118, 2989, 2935, 2826, 1583, 1497, 1458,
4-Amino-5-(4-bromophenyl)-2-[3-[4-(2-methoxyphenyl)-1
- piperazinyl]propyl] - 2,4 - dihydro - 3H[1,2,4]triazole - 3 -
thione (12m). Flash chromatography purification gave
0.20 g (20%) of 12m as a colourless oil; IR (KBr) 3273,
2930, 2814, 1593, 1497, 1451, 1238, 1010, 746 (cmꢀ1);
1H NMR (DMSO-d6) d 8.06–7.90 (m, 2H), 7.85–7.70
(m, 2H), 7.01–6.77 (m, 4H), 5.8931 (br s, 2H), 4.24 (t,
J=6.8 Hz, 2H), 3.76 (s, 3H), 3.10–2.75 (m, 4H), 2.65–
2.32 (m, 6H), 2.13–1.85 (m, 2H).
1
1231, 1026, 751 (cmꢀ1); H NMR (DMSO-d6) d 7.65–
7.55 (m, 2H), 7.52–7.38 (m, 1H), 7.18–7.07 (m, 1H),
7.00–6.78 (m, 4H), 5.8931 (br s, 2H), 4.24 (t, J=7.0, 2H),
3.80 (s, 3H), 3.75 (s, 3H), 3.10–2.73 (m, 4H), 2.65–2.28
(m, 6H), 2.10–1.85 (m, 2H).
4-Amino-5-(3-methoxyphenyl)-2-[3-[4-(2-nitrophenyl)-1-pi-
perazinyl]propyl] - 2,4 - dihydro - 3H[1,2,4]triazole - 3 - thione
(12h). Flash chromatography purification gave 0.19 g
(20%) of 12h as a yellow solid: mp 145–147 ꢃC; IR
(KBr) 3318, 2934, 2825, 1609, 1522, 1456, 1339, 1229,
1040, 747 (cmꢀ1); 1H NMR (DMSO-d6) d 7.79–7.68 (m,
1H), 7.62–7.35 (m, 4H), 7.33–7.20 (m, 1H), 7.15–7.00
(m, 2H), 5.8531 (br s, 2H), 4.20 (t, J=7.0, 2H), 3.77 (s,
3H), 3.08–2.85 (m, 4H), 2.65–2.30 (m, 6H), 2.06–1.84
(m, 2H).
4-Amino-5-(4-bromophenyl)-2-[3-[4-(2-nitrophenyl)-1-pi-
perazinyl]propyl]-2,4-dihydro-3H[1,2,4]triazole-5-thione
(12n). Flash chromatography purification gave 0.21 g
(20%) of 12n as a yellow solid: mp 146 ꢃC; IR (KBr)
3268, 3170, 2954, 2823, 1604, 1514, 1443, 1343, 1233,
1
1012, 831, 746 (cmꢀ1); H NMR (DMSO-d6) d 7.90–
8.01 (m, 2H), 7.65–7.79 (m, 3H), 7.45–7.58 (m, 1H),
7.20–7.32 (m, 1H), 7.01–7.16 (m, 1H), 5.8531 (br s, 2H),
4.20 (t, J=7.0, 2H), 2.85–3.06 (m, 4H), 2.30–2.63 (m,
6H), 1.85–2.08 (m, 2H).
4-Amino-2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]-
5-(4-methylphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-thione
(12i). Flash chromatography purification gave 0.15 g
(17%) of 12i as a white solid: mp 114 ꢃC; IR (KBr)
4-Amino-2-[3-[4-(2-methoxyphenyl)-1-piperazinyl]propyl]
-5-(4-propyloxyphenyl)-2,4-dihydro-3H[1,2,4]triazole-3-
thione (12o). Flash chromatography purification gave
0.11 g (12%) of 12o as a white solid: mp 94 ꢃC; IR (KBr)