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J = 2.19 Hz, 1H); 7.15 (d, J = 2.37 Hz, 2H); 7.53 (t, J = 7.50 Hz, 2H);
7.60–7.67 (m, 1H); 8.06 (d, J = 3.75 Hz, 2H); MS (ESI): 357.40
(C18H17N2O4S, [M+H]+). Anal. Calcd for C18H16N2O4S: C, 60.66; H,
4.53; N, 7.86. Found: C, 60.58; H, 4.54; N, 7.88.
4.2.13. 1-(4-Bromophenyl)-2-(5-(2-hydroxy-4-methylphenyl)-
1,3,4-oxadiazol-2-ylthio) ethanone (6m)
White powder, yield 84%, mp: 237–238 °C, 1H NMR(300 MHz,
CDCl3-d6) d: 2.38 (s, 3H); 4.91 (s, 2H); 6.82 (d, J = 8.22 Hz, 1H);
6.92 (s, 1H); 7.58 (d, J = 8.04 Hz, 1H); 7.60 (d, J = 8.40 Hz, 2H);
7.92 (d, J = 8.40 Hz, 2H); 9.70 (s, 1H); MS (ESI): 406.27
(C17H14BrN2O3S, [M+H]+). Anal. Calcd for C17H13BrN2O3S: C,
50.38; H, 3.23; N, 6.91; Found: C, 50.43; H, 3.22; N, 6.89.
4.2.6. 2-(5-(2-Fluorophenyl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6f)
White powder, yield 83%, mp: 152 °C, 1H NMR(300 MHz, CDCl3-
d6) d: 4.98 (s, 2H); 7.22–7.30 (m, 3H); 7.52 (t, J = 4.58 Hz, 3H); 7.63
(d, J = 4.5 Hz,1H); 8.05 (d, J = 4.5 Hz, 2H); MS (ESI):315.33
(C16H12FN2O2S, [M+H]+). Anal. Calcd for C16H11FN2O2S: C, 61.14;
H, 3.53; N, 8.91.Found: C, 61.09; H, 3.52; N, 8.95.
4.2.14. 1-(4-Bromophenyl)-2-(5-(4-tert-butylphenyl)-1,3,4-
oxadiazol-2-ylthio) ethanone (6n)
White powder, yield 82%, mp: 145 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 1.35 (s, 9H); 4.97 (s, 2H); 6.61 (d, J = 8.97 Hz, 1H);
7.66 (t, J = 11.9 Hz, 3H); 7.93 (d, J = 8.43 Hz, 2H); 8.04 (d,
J = 6.75 Hz, 1H); 8.67 (s, 1H). MS (ESI): 432.35 (C20H20BrN2O2S,
[M+H]+). Anal. Calcd for C20H19BrN2O2S: C, 51.68; H, 3.86; N,
10.05. Found: C, 51.59; H, 3.85; N, 10.09.
4.2.7. 2-(5-(Naphthalen-1-yl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6g)
White powder, yield 83%, mp: 134 °C, 1H NMR(300 MHz, CDCl3-
d6) d: 5.03 (s, 2H); 7.52–7.70 (m, 6H); 7.93 (d, J = 3.93 Hz, 1H);
8.02–8.15 (m, 4H); 9.18 (d, J = 4.2 Hz, 1H). MS (ESI):347.40
(C20H15N2O2S, [M+H]+). Anal. Calcd for C20H14N2O2S: C, 69.35; H,
4.07; N, 8.09. Found: C, 69.31; H, 4.08; N, 8.11.
4.2.15. 1-(4-Bromophenyl)-2-(5-(4-(dimethylamino)phenyl)-
1,3,4-oxadiazol-2-ylthio) ethanone (6o)
White powder, yield 85%, mp: 197–198 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 3.55 (s, 6H); 4.97 (s, 2H); 7.51 (d, J = 8.22 Hz, 2H);
7.67 (d, J = 8.40 Hz, 2H); 7.92 (d, J = 8.43 Hz, 4H). MS (ESI):
419.31 (C18H17BrN3O2S, [M+H]+). Anal. Calcd for C18H16BrN3O2S:
C, 55.69; H, 4.44; N, 6.49. Found: C, 55.65; H, 4.45; N, 6.45.
4.2.8. 2-(5-(2-Hydroxy-4-methoxyphenyl)-1,3,4-oxadiazol-2-
ylthio)-1-phenylethanone (6h)
white powder, yield 83%, mp: 195 °C, 1H NMR(300 MHz, CDCl3-
d6) d: 3.89 (d, J = 13.5 Hz; 3H); 4.96 (s, 2H); 5.35 (s, 1H); 6.57 (d,
J = 2.61 Hz, 1H); 6.61 (s, 1H),7.54 (t, J = 4.62 Hz,2H); 7.59 (d,
J = 2.61 Hz; 1H); 7.66 (t, J = 4.44 Hz; 1H); 8.05 (d, J = 2.39 Hz; 2H).
MS (ESI): 343.37 (C17H15N2O4S, [M+H]+). Anal. Calcd for
C17H14N2O4S: C, 59.74; H, 4.22; N, 8.18. Found: C, 59.66; H,
4.23; N, 8.21.
4.2.16. 1-(4-Bromophenyl)-2-(5-(pyridin-4-yl)-1,3,4-oxadiazol-
2-ylthio)ethanone (6p)
White powder, yield 88%, mp: 162–163 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 4.96 (s, 2H); 7.68 (d, J = 8.40 Hz, 2H); 7.90–7.98 (m,
4H); 8.82 (d, 2H). MS (ESI): 377.23 (C15H11BrN3O2S, [M+H]+). Anal.
Calcd for C15H10BrN3O2S: C, 47.89; H, 2.68; N, 11.17. Found: C,
47.83; H, 2.67; N, 11.19.
4.2.9. 2-(5-(2-Aminopyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6i)
Light yellow powder, yield 83%, mp: 208 °C, 1H NMR(300 MHz,
CDCl3-d6) d: 5.01 (s, 2H); 7.12 (s, 1H); 7.23 (d, J = 5.76 Hz, 1H); 7.54
(t, J = 4.62 Hz, 3H); 7.66 (s, 2H); 8.05 (d, J = 2.11 Hz; 3H). MS
(ESI):313.25 (C15H13N4O2S, [M+H]+). Anal. Calcd for C15H12N4O2S:
C, 57.68; H, 3.87; N, 17.94. Found: C, 57.59; H, 3.88; N, 17.98.
4.2.17. 1-(4-Bromophenyl)-2-(5-(3,5-dimethoxyphenyl)-1,3,4-
oxadiazol-2-ylthio) ethanone (6q)
White powder, yield 88%, mp: 169 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 3.88 (d, J = 9.70 Hz, 6H); 4.92 (s, 2H); 6.61 (s, 1H);
7.13 (s, 2H); 7.67 (d, J = 8.43 Hz, 2H); 7.92 (d, J = 8.43 Hz, 2H). MS
(ESI): 436.29 (C18H16BrN2O4S, [M+H]+). Anal. Calcd for
C18H15BrN2O4S: C, 49.67; H, 3.47; N, 6.44. Found: C, 49.63; H,
3.49; N, 6.40.
4.2.10. 2-(5-(2-Ethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6j)
White powder, yield 87%, mp: 102 °C, 1H NMR(300 MHz, CDCl3-
d6) d: 1.56 (s, 3H); 4.13–4.20 (m, 2H); 5.01 (s, 2H); 7.00–7.06 (m,
2H); 7.44–7.55 (m, 3H); 7.65 (t, J = 7.41 Hz, 1H); 7.87–7.90 (m,
1H); 8.06 (d, J = 7.32 Hz; 2H). MS (ESI): 341.40 (C18H17N2O3S,
[M+H]+). Anal. Calcd for C18H16N2O3S: C, 63.51; H, 4.74; N, 8.23.
Found: C, 63.54; H, 4.75; N, 8.21.
4.2.18. 1-(4-Bromophenyl)-2-(5-(2-fluorophenyl)-1,3,4-
oxadiazol-2-ylthio)ethanone (6r)
White powder, yield 88%, mp: 147 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 4.98 (s, 2H); 7.20–7.31 (m, 2H); 7.52 (t,
J = 5.85 Hz,1H); 7.67 (d, J = 8.43 Hz, 2H); 7.92 (d, J = 8.43 Hz, 2H);
7.99 (t, J = 7.32 Hz, 1H). MS (ESI): 394.23 (C16H11BrFN2O2S,
[M+H]+). Anal. Calcd for C16H10BrFN2O2S: C, 48.87; H, 2.56; N,
7.12. Found: C, 48.80; H, 2.57; N, 7.17.
4.2.11. 2-(5-(2-Chloropyridin-4-yl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6k)
White powder, yield 81%, mp: 165 °C, 1H NMR(300 MHz, CDCl3-
d6) d:5.01 (s, 2H); 7.54 (t, J = 4.62 Hz, 2H); 7.67 (t, J = 4.44 Hz, 1H);
7.81 (s, 1H); 7.90 (s, 1H); 8.06 (d, J = 4.50 Hz; 2H); 8.57 (s, 1H). MS
(ESI): 332.78 (C15H11ClN3O2S, [M+H]+). Anal. Calcd for
4.2.19. 1-(4-Bromophenyl)-2-(5-(naphthalen-1-yl)-1,3,4-
oxadiazol-2-ylthio)ethanone (6s)
C
15H10ClN3O2S: C, 54.40; H, 3.04; N, 12.67; Found: C, 54.36; H,
White powder, yield 85%, mp: 153–154 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 4.98 (s, 2H); 7.56–7.71 (m, 5H); 7.95 (t, J = 4.57 Hz,
3H); 8.05 (d, J = 8.25 Hz, 1H); 8.14 (d, J = 7.11 Hz, 1H); 9.18 (d,
J = 8.61 Hz, 1H). MS (ESI): 426.30 (C20H14BrN2O2S, [M+H]+). Anal.
Calcd for C20H13BrN2O2S: C, 56.48; H, 3.08; N, 6.59. Found: C,
56.44; H, 3.07; N, 6.61.
3.05; N, 12.69.
4.2.12. 2-(5-(2-Methoxyphenyl)-1,3,4-oxadiazol-2-ylthio)-1-
phenylethanone (6l)
White powder, yield 89%, mp: 153 °C, 1H NMR(300 MHz, CDCl3-
d6) d: 3.94 (s, 3H); 4.98 (s, 2H); 7.05 (t, J = 8.60 Hz, 2H); 7.47–7.55
(m, 3H); 7.64 (t, J = 9.60 Hz, 1H); 7.87 (d, J = 7.68 Hz, 1H); 8.06 (d,
J = 7.5 Hz, 2H). MS (ESI): 327.37 (C17H15N2O3S, [M+H]+). Anal. Calcd
for C17H14N2O3S: C, 62.56; H, 4.32; N, 8.58.Found: C, 62.52; H, 4.30;
N, 8.61.
4.2.20. 1-(4-Bromophenyl)-2-(5-(2-hydroxy-4-methoxyphenyl)-
1,3,4-oxadiazol-2-ylthio)ethanone (6t)
White powder, yield 86%, mp: 229–230 °C, 1H NMR (300 MHz,
CDCl3-d6) d: 3.89 (d, J = 7.64 Hz, 3H); 4.98 (s, 2H); 5.35 (s, 1H);