0 %, mp: 136–140 °C (dec ) Analysis for C24H20N6S2 (456 58); cal

0 %, mp: 136–140 °C (dec.). Analysis for C24H20N6S2 (456.58); calculated: C, 63.13; H, 4.41; N, 18.41; S, 14.04; found: C, 63.26; H, 4.42; N, 18.35; S, Selleckchem IWR1 14.08. IR (KBr), ν (cm−1): 3155 (NH), 3091 (CH aromatic) 2961, 1453, 762 (CH aliphatic), 1609 (C=N), 1508

(C–N), 1342 (C=S), 677 (C–S). 1H NMR (DMSO-d 6) δ (ppm): 4.29 (s, 2H, CH2), 5.24 (s, 2H, CH2), 7.22–7.53 (m, 15H, 15ArH), 13.86 (brs, 1H, NH). 4-(4-Methoxybenzyl)-5-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]methyl-4H-1,2,4-triazole-3(2H)-thione (5i) Yield: 98.5 %, mp: 118–120 °C (dec.). Analysis for C25H22N6OS2 (486.61); calculated: C, 61.70; H, 4.56; N, 17.27; S, 13.18; found: C, 61.61; H, 4.55; N, 17.25; S, 13.14. IR (KBr), ν (cm−1): 3174 (NH), 3071 (CH aromatic), 2982, 1453, 764 (CH aliphatic), Stattic cell line 1612 (C=N), 1510 (C–N), 1358 (C=S),

673 (C–S). 1H NMR (DMSO-d 6) δ (ppm): 3.71 (s, 3H, CH3), 4.33 (s, 2H, CH2), 5.20 (s, 2H, CH2), 6.83–7.52 (m, 14H, 14ArH), 13.82 (brs, 1H, NH). Derivatives of 2,5-disubstituted-1,3,4-thiadiazole (6a–i) Method A (for compounds 6a–i) 10 mmol of 4-substituted-1-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl thiosemicarbazide 4a–i was dissolved in 10–20 mL diluted sulfuric acid and stirred in a closed bulb for 1 h. Subsequently, the solution was poured out on crushed ice (50 g) and stirred until the ice was completely dissolved. Later, the solution was neutralized with ammonium hydroxide. The TPCA-1 precipitate that formed was filtered, dried, and crystallized from ethanol 6a, c, d, g–i or butanol 6b, e, f. Method B (for compounds 6a, d) 20 mL of 10 % ethanolic solution of hydrochloric acid was added to thiosemicarbazide 4a, d and the reaction mixture was heated under reflux for 1 h. Subsequently, the solution was left at room temperature for 24 h. The precipitate formed was separated by filtration, dried, and crystallized from ethanol. Method

C (for compounds PRKACG 6e, f) A mixture of 10 mmol of thiosemicarbazide 4e, f in 10 mL of anhydrous acetic acid was refluxed for 1 h. Subsequently, the solution was left at room temperature for 12 h. The precipitate that formed was separated by filtration, dried, and crystallized from butanol. 5-Aminoethyl-2-[(4,5-diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]methyl-1,3,4-thiadiazole (6a) Yield: 81.3 %, mp: 168–170 °C (dec.). Analysis for C19H18N6S2 (394.52); calculated: C, 57.84; H, 4.60; N, 21.30; S, 16.25; found: C, 57.69; H, 4.58; N, 21.26; S, 16.21. IR (KBr), ν (cm−1): 3244 (NH), 3071 (CH aromatic), 2944, 1458, 733 (CH aliphatic), 1602 (C=N), 1506 (C–N), 671 (C–S). 1H NMR (DMSO-d 6) δ (ppm): 1.13 (t, J = 7.5 Hz, 3H, CH3), 3.21–3.27 (q, J = 5 Hz, J = 5 Hz, 2H, CH2), 4.57 (s, 2H, CH2), 7.17–7.70 (m, 10H, 10ArH), 9.35 (brs, 1H, NH).

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