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(m, 2H), 7.50–7.55 (m, 2H), 7.64–7.67 (m, 1H), 10.25 (s, 1H). MS
4.2.14. 2-(5-(Benzylthio)-1,3,4-oxadiazol-2-yl)-5-methylphenol
(6n)
(ESI): 333.06 (C16H14FN2O3S, [M+H]+). Anal. Calcd for C16H13
FN2O3S: C, 57.82; H, 3.94; N, 8.43; Found: C, 57.87; H, 3.92; N, 8.44.
White crystal, yield 77%, mp: 103–104 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.56 (s, 2H), 6.83 (d, J = 8.0 Hz, 1H),
6.88 (s, 1H), 7.26–7.37 (m, 3H), 7.48 (d, J = 6.8 Hz, 2H), 7.61 (d,
J = 8.0 Hz, 1H), 10.09 (s, 1H). MS (ESI): 299.08 (C16H15N2O2S,
[M+H]+). Anal. Calcd for C16H14N2O2S: C, 64.41; H, 4.73; N, 9.39;
Found: C, 64.45; H, 4.74; N, 9.35.
4.2.7. 5-Methoxy-2-(5-((3-methylbenzyl)thio)-1,3,4-oxadiazol-
2-yl)phenol (6g)
White crystal, yield 64%, mp: 99–100 °C. 1H NMR (300 MHz, d6-
DMSO) d: 2.28 (s, 3H), 3.80 (s, 3H), 4.51 (s, 2H), 6.60–6.62 (m, 2H),
7.10 (d, J = 7.0 Hz, 1H), 7.20–7.28 (m, 3H), 7.64–7.67 (m, 1H), 10.24
(s, 1H). MS (ESI): 329.09 (C17H17N2O3S, [M+H]+). Anal. Calcd for
4.2.15. 2-(5-((2-Chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-
methylphenol (6o)
C17H16N2O3S: C, 62.18; H, 4.91; N, 8.53; Found: C, 62.22; H, 4.90;
White powder, yield 79%, mp: 148–149 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.63 (s, 2H), 6.83 (d, J = 8.0 Hz, 1H),
6.89 (s, 1H), 7.31–7.39 (m, 2H), 7.49–7.52 (m, 1H), 7.60–7.64 (m,
2H), 10.11 (s, 1H). MS (ESI): 333.04 (C16H14ClN2O2S, [M+H]+). Anal.
Calcd for C16H13ClN2O2S: C, 57.74; H, 3.94; N, 8.42; Found: C,
57.78; H, 3.96; N, 8.36.
N, 8.52.
4.2.8. 5-Methoxy-2-(5-((4-methylbenzyl)thio)-1,3,4-oxadiazol-
2-yl)phenol (6h)
White crystal, yield 68%, mp: 129–130 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.27 (s, 3H), 3.80 (s, 3H), 4.51 (s, 2H), 6.60–6.63
(m, 2H), 7.14 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 7.64–7.68
(m, 1H), 10.24 (s, 1H). MS (ESI): 329.09 (C17H17N2O3S, [M+H]+).
Anal. Calcd for C17H16N2O3S: C, 62.18; H, 4.91; N, 8.53; Found: C,
62.26; H, 4.93; N, 8.50.
4.2.16. 2-(5-((3-Chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-
methylphenol (6p)
White crystal, yield 77%, mp: 130–131 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.56 (s, 2H), 6.83 (d, J = 7.7 Hz, 1H),
6.89 (s, 1H), 7.36–7.41 (m, 2H), 7.45–7.47 (m, 1H), 7.58–7.62 (m,
2H), 10.09 (s, 1H). MS (ESI): 333.04 (C16H14ClN2O2S, [M+H]+). Anal.
Calcd for C16H13ClN2O2S: C, 57.74; H, 3.94; N, 8.42; Found: C,
57.79; H, 3.96; N, 8.40.
4.2.9. 5-Methoxy-2-(5-((3-methoxybenzyl)thio)-1,3,4-oxadiazol
-2-yl)phenol (6i)
White crystal, yield 60%, mp: 97–98 °C. 1H NMR (300 MHz,
d6-DMSO) d: 3.72 (s, 3H), 3.80 (s, 3H), 4.52 (s, 2H), 6.59–6.62
(m, 2H), 6.84–6.87 (m, 1H), 7.02–7.05 (m, 2H), 7.26 (t, J = 8.2 Hz,
1H), 7.65–7.68 (m, 1H), 10.25 (s, 1H). MS (ESI): 345.08
(C17H17N2O4S, [M+H]+). Anal. Calcd for C17H16N2O4S: C, 59.29; H,
4.68; N, 8.13; Found: C, 59.34; H, 4.71; N, 8.10.
4.2.17. 2-(5-((4-Chlorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-
methylphenol (6q)
White crystal, yield 80%, mp: 142–143 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.55 (s, 2H), 6.83 (d, J = 7.9 Hz, 1H),
6.88 (s, 1H), 7.39–7.42 (m, 2H), 7.50–7.53 (m, 2H), 7.61 (d,
J = 7.9 Hz, 1H), 10.10 (s, 1H). MS (ESI): 333.04 (C16H14ClN2O2S,
[M+H]+). Anal. Calcd for C16H13ClN2O2S: C, 57.74; H, 3.94; N,
8.42; Found: C, 57.78; H, 3.93; N, 8.39.
4.2.10. 5-Methoxy-2-(5-((4-methoxybenzyl)thio)-1,3,4-oxadia-
zol-2-yl)phenol (6j)
White crystal, yield 63%, mp: 112–113 °C. 1H NMR (300 MHz,
d6-DMSO) d: 3.73 (s, 3H), 3.80 (s, 3H), 4.50 (s, 2H), 6.59–6.63
(m, 2H), 6.89 (d, J = 8.6 Hz, 2H), 7.39 (d, J = 8.6 Hz, 2H), 7.65–7.68
(m, 1H), 10.25 (s, 1H). MS (ESI): 345.08 (C17H17N2O4S, [M+H]+).
Anal. Calcd for C17H16N2O4S: C, 59.29; H, 4.68; N, 8.13; Found: C,
59.36; H, 4.71; N, 8.09.
4.2.18. 2-(5-((2-Fluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-
methylphenol (6r)
White crystal, yield 74%, mp: 118–119 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.58 (s, 2H), 6.83 (d, J=8.1 Hz, 1H), 6.89
(s, 1H), 7.15–7.26 (m, 2H), 7.33–7.41 (m, 1H), 7.53–7.59 (m, 1H),
7.61 (d, J = 8.0 Hz, 1H), 10.09 (s, 1H). MS (ESI): 317.07
(C16H14FN2O2S, [M+H]+). Anal. Calcd for C16H13FN2O2S: C, 60.75;
H, 4.14; N, 8.86; Found: C, 60.79; H, 4.15; N, 8.82.
4.2.11. 5-Methoxy-2-(5-((2-nitrobenzyl)thio)-1,3,4-oxadiazol-2-
yl)phenol (6k)
Light yellow crystal, yield 60%, mp: 127–128 °C. 1H NMR
(300 MHz, d6-DMSO) d: 3.80 (s, 3H), 4.81 (s, 2H), 6.60–6.63
(m, 2H), 7.58–7.66 (m, 2H), 7.73–7.81 (m, 2H), 8.12 (d, J = 8.0 Hz,
1H), 10.26 (s, 1H). MS (ESI): 360.06 (C16H14N3O5S, [M+H]+). Anal.
Calcd for C16H13N3O5S: C, 53.48; H, 3.65; N, 11.69; Found: C,
53.53; H, 3.66; N, 11.66.
4.2.19. 2-(5-((4-Fluorobenzyl)thio)-1,3,4-oxadiazol-2-yl)-5-
methylphenol (6s)
White crystal, yield 75%, mp: 125–126 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.31 (s, 3H), 4.55 (s, 2H), 6.83 (d, J = 7.9 Hz, 1H),
6.88 (s, 1H), 7.14–7.21 (m, 2H), 7.51–7.55 (m, 2H), 7.61 (d,
J = 7.9 Hz, 1H), 10.10 (s, 1H). MS (ESI): 317.07 (C16H14FN2O2S,
[M+H]+). Anal. Calcd for C16H13FN2O2S: C, 60.75; H, 4.14; N, 8.86;
Found: C, 60.79; H, 4.16; N, 8.81.
4.2.12. 5-Methoxy-2-(5-((3-nitrobenzyl)thio)-1,3,4-oxadiazol-2-
yl)phenol (6l)
Brown crystal, yield 65%, mp: 132–133 °C. 1H NMR (300 MHz, d6-
DMSO) d: 3.80 (s, 3H), 4.69 (s, 2H), 6.57–6.60 (m, 2H), 7.63–7.68
(m, 2H), 7.96 (d, J = 7.9 Hz, 1H), 8.14–8.17 (m, 1H), 8.40(t,
J = 2.0 Hz, 1H), 10.24 (s, 1H). MS (ESI): 360.06 (C16H14N3O5S,
[M+H]+). Anal. Calcd for C16H13N3O5S: C, 53.48; H, 3.65; N, 11.69;
Found: C, 53.52; H, 3.63; N, 11.68.
4.2.20. 5-Methyl-2-(5-((3-methylbenzyl)thio)-1,3,4-oxadiazol-
2-yl)phenol (6t)
4.2.13. 5-Methoxy-2-(5-((4-nitrobenzyl)thio)-1,3,4-oxadiazol-2-
yl)phenol (6m)
White crystal, yield 72%, mp: 115–116 °C. 1H NMR (300 MHz,
d6-DMSO) d: 2.28 (s, 3H), 2.31 (s, 3H), 4.52 (s, 2H), 6.83 (d,
J = 8.0 Hz, 1H), 6.89 (s, 1H), 7.10 (d, J = 6.8 Hz, 1H), 7.20–7.29 (m,
3H), 7.61 (d, J = 7.9 Hz, 1H), 10.09 (s, 1H). MS (ESI): 313.09
(C17H17N2O2S, [M+H]+). Anal. Calcd for C17H16N2O2S: C, 65.36; H,
5.16; N, 8.97; Found: C, 65.41; H, 5.18; N, 8.94.
Yellow crystal, yield 67%, mp: 166–167 °C. 1H NMR (300 MHz, d6-
DMSO) d: 3.79 (s, 3H), 4.67 (s, 2H), 6.58–6.62 (m, 2H), 7.63–7.66 (m,
1H), 7.77 (d, J=8.8 Hz, 2H), 8.21 (d, J = 8.8 Hz, 2H), 10.24 (s, 1H). MS
(ESI): 360.06 (C16H14N3O5S, [M+H]+). Anal. Calcd for C16H13N3O5S:
C, 53.48; H, 3.65; N, 11.69; Found: C, 53.54; H, 3.63; N, 11.65.