30 (s, 2H, selleck chemical CH2), 7.17 (d, 2H, Ar–H, J = 8.89 Hz), 7.22–7.32 (m, 4H, Ar–H), 7.62 (d, 2H, Ar–H, J = 8.90 Hz). IR (KBr, ν, cm−1): 3030, 2986, 2832, 1603, 1541, 1341, 813. Anal. Calc. for C19H20BrClN4S (%): C 50.51, H 4.46, N 12.40. Found: C 50.41, H 4.38, N 12.29. 4-(4-Bromophenyl)-5-(2-chlorophenyl)-2-(pyrrolidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (15) Yield: 84 %,
m.p. 143–145 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.76–1.83 (m, 4H, 2 × CH2), 2.96 (t, 4H, 2 × CH2, J = 6.40 Hz), 5.32 (s, 2H, CH2), 7.17 (d, 2H, Ar–H, J = 8.75 Hz), 7.22–7.30 (m, 4H, Ar–H), 7.63 (d, 2H, Ar–H, J = 8.75 Hz). IR (KBr, ν, cm−1): 3099, 2956, 2825, 1589, 1530, 1327, 802. Anal. Calc. for C19H18BrClN4S (%): C 50.73, H 4.03, N 12.46. Found: C 50.66, H 4.12, N 12.45. 4-(4-Bromophenyl)-5-(2-chlorophenyl)-2-(piperidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (16) Yield: 80 %, m.p. 180–181 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.36–1.69 (m, 6H, 3 × CH2), 2.85 (t, 4H,
2 × CH2, J = 5.40 Hz), 5.22 (s, 2H, CH2), 7.18 (d, 2H, Ar–H, J = 8.71 Hz), 7.23–7.34 (m, 4H, Ar–H), 7.63 (d, 2H, Ar–H, J = 8.70 Hz). IR (KBr, ν, cm−1): 3062, 2985, 2800, 1594, 1526, 1342, 784. Anal. Calc. for C20H20BrClN4S (%): C 51.79, H 4.35, N 12.08. Metabolism inhibitor Found: C 51.90, H 4.35, N 12.00. 4-(4-Bromophenyl)-5-(2-chlorophenyl)-2-(morpholin-4-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (17) Yield: 76 %, m.p. 174–175 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 2.91 (t, 4H, 2 × CH2, J = 4.75 Hz), 3.72 (t, 4H, 2 × CH2, J = 4.75 Hz), 5.23 (s, 2H, CH2), 7.17 (d, 2H, Ar–H, J = 8.81 Hz), 7.23–7.34 (m, 4H, Ar–H), 7.64 (d, 2H, Ar–H, J = 8.81 Hz). IR (KBr, ν, cm−1): 3037, 2903, 2785, 1600, 1521, 1328, 806. Anal. Calc. for C19H18BrClN4OS (%): C 48.99, H 3.90, N 12.03. Found: C 49.11, H 3.84, N 12.17. 4-(4-Bromophenyl)-5-(4-chlorophenyl)-2-[(diethylamino)methyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione (18) Yield: 82 %, m.p. 175–176 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.20 (t, 6H, 2 × CH3,
J = 7.24 Hz), 2.90 (q, 4H, 2 × CH2, J = 7.24 Hz), 5.30 (s, 2H, CH2), 7.17 (d, 2H, Ar–H, J = 8.63 Hz), 7.22–7.33 (m, 4H, Ar–H), 7.62 (d, 2H, Ar–H, J = 8.63 Hz). 4-(4-Bromophenyl)-5-(4-chlorophenyl)-2-(pyrrolidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione Oxalosuccinic acid (19) Yield: 87 %, m.p.