General procedure for the synthesis of Mannich bases (10–21) 10 mmol of the 1,2,4-triazole derivative (7–9) was dissolved (with heating) in 20 ml of anhydrous ethanol and then equimolar amounts of appropriate secondary amine (diethylamine, pyrrolidine, piperidine, and morpholine) and formaldehyde solution (37 %)

were added. The obtained mixture was stirred at room temperature for 30 min. Next, 5 ml of distilled water was added, the precipitate was filtered off, washed with distilled water, and recrystallized ABT-263 molecular weight from ethanol. 4-(4-Bromophenyl)-2-[(diethylamino)methyl]-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione Selleck JPH203 (10) Yield: 78 %, m.p. 118–120 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.20 (t, 6H, 2 × CH3, J = 7.17 Hz), 2.90 (q, 4H, 2 × CH2, J = 7.18 Hz), 5.32 (s, 2H, CH2), 7.18 (d, 2H, Ar–H, J = 8.69 Hz), 7.25–7.34 (m, 5H, Ar–H), 7.61 (d, 2H, Ar–H, J = 8.70 Hz). IR (KBr, ν, cm−1):

3065, 2931, 2796, 1612, 1520, 1331, 799. Anal. Calc. for C19H21BrN4S (%): C 54.68, H 5.07, N 13.42. Found: C 54.60, H 5.02, N 13.53. 4-(4-Bromophenyl)-5-phenyl-2-(pyrrolidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (11) Yield: 82 %, m.p. 142–143 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.75–1.83 (m, 4H, 2 × CH2), 2.99 (t, 4H, 2 × CH2, J = 6.43 Hz), 5.34 (s, 2H, CH2), 7.19 (d, 2H, Ar–H, J = 8.86 Hz), 7.25–7.33 (m, 5H, Ar–H), 7.61 (d, 2H, Ar–H, J = 8.84 Hz). IR (KBr, ν, cm−1): 3084, 3008, 2915, 2868, 1584, 1513, 1323, 806. Anal. Calc. for C19H19BrN4S (%): C 54.94, H 4.61, N 13.49. Found: C 55.05, H 4.50, 13.50. 4-(4-Bromophenyl)-5-phenyl-2-(piperidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

(12) Yield: 77 %, m.p. 122–123 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 1.44–1.68 (m, 6H, 3 × CH2), 2.87 (t, 4H, 2 × CH2, J = 5.40 Hz), 5.25 (s, 2H, CH2), 7.19 (d, 2H, Ar–H, J = 8.90 Hz), 7.24–7.35 (m, 5H, Ar–H), 7.61 (d, 2H, Ar–H, J = 8.90 Hz). IR (KBr, ν, cm−1): 3110, 2918, 2785, 1603, 1519, 1342, 808. Anal. Calc. for C20H21BrN4S (%): C 55.94, H 4.93, N 13.05. Found: C 56.00, H 4.90, N 13.17. 4-(4-Bromophenyl)-2-(morpholin-4-ylmethyl)-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (13) Yield: 83 %, m.p. 146–147 °C, 1H-NMR (250 MHz) (CDCl3) δ (ppm): 2.95 (t, Cytidine deaminase 4H, 2 × CH2, J = 4.26 Hz), 3.76 (t, 4H, 2 × CH2, J = 4.26 Hz), 5.26 (s, 2H, CH2), 7.18 (d, 2H, Ar–H, J = 8.80 Hz), 7.24–7.35 (m, 5H, Ar–H), 7.62 (d, 2H, Ar–H, J = 8.81 Hz). IR (KBr, ν, cm−1): 3074, 3021, 2961, 2831, 1574, 1512, 1328, 786.