Med Chem Res
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3-Phenyl-4-amino-5-(n-hexyldisulfanyl)-1,2,4-triazole
(8g) White solid, Yield 51%, m.p.: 103.8–104.5 °C. IR
(KBr, cm–1): 3474, 3413, 3134, 2362, 1638, 1618, 1453,
1275, 1243, 1232, 1014, 974, 904, 828, 767, 683. H NMR
(DMSO-d6, 400 MHz) δ (ppm): 8.09 (d, J = 8.4 Hz, 2H,
Ar–H), 7.63 (d, J = 8.4 Hz, 2H, Ar–H), 6.28 (s, 2H, NH2),
2.96 (t, J = 7.2 Hz, 2H, SCH2), 1.71–1.80 (m, 2H, CH2),
0.96 (t, J = 7.2 Hz, 3H, CH3). 13C NMR (DMSO-d6, 100
MHz) δ (ppm): 153.88, 153.34, 135.29, 130.13, 129.13,
126.04, 41.11, 21.94, 13.19. HR-ESI-MS (m/z): Calcd for
C11H13ClN4S2: 301.0349 [M + H]+, Found 301.0348.
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1401, 975, 769, 690. H NMR (DMSO-d6, 400 MHz) δ
(ppm): 8.03–8.05 (m, 2H, Ar–H), 7.53–7.55 (m, 3H, Ar–H),
6.25 (s, 2H, NH2), 2.99 (d, J = 7.2 Hz, 2H, SCH2),
1.69–1.76 (m, 2H, CH2), 1.25–1.37 (m, 6H, CH2), 0.86 (t, J
= 6.8 Hz, 3H, CH3). 13C NMR (DMSO-d6, 100 MHz) δ
(ppm): 154.56, 153.57, 129.40, 128.95, 128.45, 127.36,
38.65, 31.26, 28.47, 27.80, 22.44, 14.32. HR-ESI-MS (m/
z): Calcd for C14H20N4S2: 309.1208 [M + H]+, Found
309.1210.
3-(4-Chlorophenyl)-4-amino-5-(i-propyldisulfanyl)-1,2,4-
triazole (8l) Pale yellow solid, Yield 51%, m.p.:
115.6–116.9 °C. IR (KBr, cm–1): 3474, 3413, 3134, 2863,
2360, 2027, 1638, 1618, 1474, 1447, 1401, 1154, 1014,
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3-Phenyl-4-amino-5-benzyldisulfanyl-1,2,4-triazole (8h)
White solid, Yield 51%, m.p.: 129.3–130.6 °C. IR (KBr,
cm–1): 3475, 3413, 3144, 2360, 1638, 1618, 1469, 1453,
975, 950, 931, 832, 768, 749, 725, 695, 682. H NMR
(DMSO-d6, 400 MHz) δ (ppm): 8.09 (d, J = 8.8 Hz, 2H,
Ar–H), 7.63 (d, J = 8.4 Hz, 2H, Ar–H), 6.27 (s, 2H, NH2),
3.38 (m, 1H, SCH), 1.34 (d, J = 6.8 Hz, 6H, CH3). 13C
NMR (DMSO-d6, 100 MHz) δ (ppm): 153.82, 153.51,
135.26, 130.12, 129.13, 126.05, 41.68, 22.46. HR-ESI-MS
(m/z): Calcd for C11H13ClN4S2: 301.0349 [M + H]+, Found
301.0350.
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1401, 1238, 1137, 970, 863, 773, 764, 715, 695. H NMR
(DMSO-d6, 400 MHz) δ (ppm): 8.04–8.07 (m, 2H, Ar–H),
7.54–7.57 (m, 3 H, Ar–H), 7.28–7.43 (m, 5H, Ar–H), 6.25
(s, 2H, NH2), 4.27 (s, 2H, SCH2). 13C NMR (DMSO-d6,
100 MHz) δ (ppm): 154.88, 153.05, 137.07, 130.45, 129.99,
129.01, 128.97, 128.50, 128.02, 127.19, 42.55. HR-ESI-MS
(m/z): Calcd for C15H14N4S2: 315.0738 [M + H]+, Found
315.0742.
3-(4-Chlorophenyl)-4-amino-5-(n-butyldisulfanyl)-1,2,4-
triazole (8m) White solid, Yield 53%, m.p.: 104.5–105.9 °C.
IR (KBr, cm–1): 3475, 3414, 3126, 2956, 2929, 2360, 2027,
1638, 1618, 1452, 1401, 1273, 1243, 1220, 1114, 996, 834,
747, 730, 681. 1H NMR (DMSO-d6, 400 MHz) δ (ppm): 8.09
(d, J = 8.8 Hz, 2H, Ar–H), 7.63 (d, J = 8.4 Hz, 2H, Ar–H),
6.27 (s, 2H, NH2), 2.99 (t, J = 7.2 Hz, 2H, SCH2), 1.68–1.75
(m, 2H, CH2), 1.34–1.43 (m, 2H, CH2), 0.89 (t, J = 7.2 Hz,
3H, CH3). 13C NMR (DMSO-d6, 100 MHz) δ (ppm): 153.88,
153.34, 135.29, 130.12, 129.13, 126.05, 38.40, 30.63, 21.36,
13.95. HR-ESI-MS (m/z): Calcd for C12H15ClN4S2: 315.0505
[M + H]+, Found 315.0504.
3-Phenyl-4-amino-5-(4-chlorobenzyldisulfanyl)-1,2,4-tria-
zole (8i) White solid, Yield 48%, m.p.: 148.4–149.8 °C.
IR (KBr, cm–1): 3475, 3413, 3147, 1656, 1595, 1489, 1465,
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1402, 991, 837, 825, 804, 772, 739, 718, 693. H NMR
(DMSO-d6, 400 MHz) δ (ppm): 8.04–8.06 (m, 2H, Ar–H),
7.54–7.56 (m, 3H, Ar–H), 7.41–7.47 (AB × 2, JAB = 8.8
Hz, 4H, Ar–H), 6.26 (s, 2H, NH2), 4.25 (s, 2H, SCH2). 13
C
NMR (DMSO-d6, 100 MHz) δ (ppm): 155.04, 153.93,
136.18, 134.55, 131.71, 130.89, 129.40, 128.96, 128.49,
126.26, 41.38. HR-ESI-MS (m/z): Calcd for C15H13ClN4S2:
349.0349 [M + H]+, Found 349.0352.
3-(4-Chlorophenyl)-4-amino-5-(i-butyldisulfanyl)-1,2,4-
triazole (8n) Pale yellow solid, Yield 48%, m.p.:
101.2–103.1 °C. IR (KBr, cm–1): 3473, 3413, 3137, 2966,
2870, 2360, 1638, 1618, 1472, 1449, 1401, 1242, 1014,
3-(4-Chlorophenyl)-4-amino-5-ethyldisulfanyl-1,2,4-tria-
zole (8j) Pale yellow solid; Yield 48%, m.p.: 107.6–109.2
°C. IR (KBr, cm–1): 3474, 3414, 3146, 2361, 1638, 1618,
1474, 1448, 1401, 1276, 1244, 1012, 974, 925, 833, 782,
768, 751, 724, 681. 1H NMR (DMSO-d6, 400 MHz) δ
(ppm): 8.09 (d, J = 8.4 Hz, 2H, Ar–H), 7.63 (d, J = 8.8 Hz,
2H, Ar–H), 6.28 (s, 2H, NH2), 2.96–3.02 (q, J = 7.2 Hz,
2H, SCH2), 1.35 (t, J = 7.2 Hz, 3H, CH3). 13C NMR
(DMSO-d6, 100 MHz) δ (ppm): 153.89, 153.39, 135.28,
130.13, 129.13, 126.05, 32.74, 14.43. HR-ESI-MS (m/z):
Calcd for C10H11ClN4S2: 287.0192 [M + H]+, Found
287.0195.
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946, 829, 767, 750, 725, 695, 682. H NMR (DMSO-d6,
400 MHz) δ (ppm): 8.09 (d, J = 8.4 Hz, 2H, Ar–H), 7.63 (d,
J = 8.4 Hz, 2H, Ar–H), 6.28 (s, 2H, NH2), 2.90 (d, J = 6.8
Hz, 2H, SCH2), 1.98–2.10 (m, 1H, CH), 0.97 (d, J = 6.8
Hz, 6H, CH3). 13C NMR (DMSO-d6, 100 MHz) δ (ppm):
153.89, 153.30, 135.28, 130.12, 129.14, 126.06, 47.81,
27.78, 21.83. HR-ESI-MS (m/z): Calcd for C12H15ClN4S2:
315.0505 [M + H]+, Found 315.0502.
3-(4-Chlorophenyl)-4-amino-5-(n-pentyldisulfanyl)-1,2,4-
triazole (8o) White solid, Yield 50%, m.p.: 107.7–109.3 °C.
IR (KBr, cm–1): 3473, 3414, 3128, 2926, 2857, 2361, 2342,
2027, 1638, 1618, 1452, 1401, 1273, 1244, 1093, 995, 952,
833, 747, 730, 690. 1H NMR (DMSO-d6, 400 MHz) δ (ppm):
3-(4-Chlorophenyl)-4-amino-5-(n-propyldisulfanyl)-1,2,4-
triazole (8k) White solid, Yield 48%, m.p.: 110.4–112.3 °C.
IR (KBr, cm–1): 3473, 3413, 3133, 2360, 1638, 1618, 1401,