Biphenyltetrazole Derivatives with 1,3,4-Oxadiazole
J. Chin. Chem. Soc., Vol. 52, No. 3, 2005 541
Table 2. 1H NMR data of compounds 6a-6i
No.
1H NMR (d, ppm)
6a
6b
6c
6d
6e
6f
8.01-7.98 (m, 3H, ArH), 7.48 (dd, J = 6.9, 2.7 Hz, 5H, ArH), 7.36-7.08 (m, 14H, ArH), 6.88
(d, J = 9.0 Hz, 6H, ArH), 4.44 (s, 2H, SCH2).
8.80 (d, J = 4.5 Hz, 2H, ArH), 7.97 (dd, J = 6.6, 2.4 Hz, 1H, ArH), 7.84 (d, J = 4.8 Hz, 2H,
ArH), 7.50-7.10 (m, 16H, ArH), 6.90 (d, J = 7.2 Hz, 6H, ArH), 4.46 (s, 2H, SCH2).
7.98 (d, J = 8.1 Hz, 1H, ArH), 7.86 (dd, J = 7.5, 1.8 Hz, 1H, ArH), 7.75 (d, J = 8.4 Hz, 1H,
ArH), 7.50-7.09 (m, 18H, ArH), 6.90 (d, J = 7.2 Hz, 6H, ArH), 4.44 (s, 2H, SCH2).
7.99-7.96 (m, 1H, ArH), 7.86 (dd, J = 8.7, 2.4 Hz, 2H, ArH), 7.64 (dd, J = 8.1, 1.8 Hz, 2H,
ArH), 7.50-7.08 (m, 16H, ArH), 6.89 (dd, J = 7.8, 1.2 Hz, 6H, ArH), 4.43 (s, 2H, SCH2).
7.98 (dd, J = 4.5, 1.8 Hz, 1H, ArH), 7.86 (dd, J = 8.1, 1.8 Hz, 1H, ArH), 7.51-7.03 (m, 19H,
ArH), 6.90 (dd, J = 7.2, 1.2 Hz, 6H, ArH), 4.43 (s, 2H), 3.93(s, 3H, SCH2).
7.98 (d, J = 7.5 Hz, 1H, ArH), 7.58-7.04 (m, 20H, ArH), 6.90 (d, J = 7.8 Hz, 6H, ArH), 4.43 (s,
2H, SCH2), 3.87 (s, 3H, CH3O).
6g
6h
6i
7.98-7.96 (m, 2H, ArH), 7.89 (d, J = 7.5 Hz, 1H, ArH), 7.52-7.08 (m, 18H, ArH), 6.89 (d, J =
7.8 Hz, 6H, ArH), 4.43 (s, 2H, SCH2).
7.98 (dd, J = 5.1, 1.8 Hz, 1H, ArH), 7.83-7.78 (t, J = 7.9 Hz, 2H, ArH), 7.50-7.09 (m, 18H,
ArH), 6.91-6.88 (dd, J = 7.2, 1.2 Hz, 6H, ArH), 4.43 (s, 2H, SCH2), 2.43 (s, 3H, CH3).
7.99-7.87 (m, 2H, ArH), 7.49-7.11 (m, 19H, ArH), 7.10-6.98 (d, J = 7.8 Hz, 6H, ArH), 4.42 (s,
2H, SCH2), 2.42 (s, 3H, CH3).
Table 3. 1H NMR data of compounds 7a-7i
No.
1H NMR (d, ppm)
7a
7.89 (dd, J = 7.5, 1.2 Hz, 2H, ArH), 7.60-7.33 (m, 9H, ArH), 7.04 (d, J = 8.1 Hz, 2H,
ArH), 4.44 (s, 2H, CH2S).
7b
7c
7d
7e
7f
8.73 (s, 2H, ArH), 7.78-7.18 (m, 8H, ArH), 7.04 (d, J = 6.3 Hz, 2H, ArH), 4.51 (s, 2H,
CH2S).
7.77 (dd, J = 7.5, 1.8 Hz, 1H, ArH), 7.67 (d, J = 7.5 Hz, 1H, ArH), 7.61-7.32 (m, 8H,
ArH), 7.04 (d, J = 8.1 Hz, 2H, ArH), 4.46 (s, 2H, CH2S).
7.78 (d, J = 8.4 Hz, 2H, ArH), 7.71-7.29 (m, 8H, ArH), 7.03 (d, J = 7.5 Hz, 2H, ArH),
4.45 (s, 2H, CH2S).
7.74 (dd, J = 7.5, 1.2 Hz, 1H, ArH), 7.60-7.31 (m, 7H, ArH), 7.04-6.96 (m, 4H, ArH),
4.43 (s, 2H, CH2S), 3.84 (s, 3H, OCH3).
7.81 (dd, J = 8.7, 1.8 Hz, 1H, ArH), 7.59-7.33 (m, 7H, ArH), 7.04-6.96 (m, 4H, ArH),
4.45 (s, 2H, CH2S), 3.80 (s, 3H, OCH3).
7g
7h
7i
7.87-7.80 (m, 2H, ArH), 7.60-7.33 (m, 8H, ArH), 7.04 (d, J = 8.1 Hz, 2H, ArH), 4.50
(s, 2H, CH2S).
7.71-7.30 (m, 10H, ArH), 7.05 (d, J = 8.7 Hz, 2H, ArH), 4.51 (s, 2H, CH2S), 2.36 (s,
3H, CH3).
7.76 (d, J = 8.1 Hz, 2H, ArH), 7.61-7.23 (m, 8H, ArH), 7.04 (d, J = 7.8 Hz, 2H, ArH),
4.43 (s, 2H, CH2S), 2.34 (s, 3H, CH3).
cm-1 and 1216-1258 cm-1, respectively. The molecular ions of
7a-7i could be detected by FAB-MS.
fect to these bacteria. The investigation on the structure-
activity relationship shows that chlorine enhances the anti-
bacterial action of the title compounds. Further investigation
on the biological activity of these compounds is in progress.
Compounds 7a-7i were screened for their antibacterial
activity against Escherichia coli, Bacillus subtilis, Staphylo-
coccus aureu and Streptococcus employing the cup-plate
method at the concentration of 100 mg/mL in nutrient agar
media.13 The results are listed in Table 6. The antibacterial ac-
tivity showed that most of the compounds were active against
microorganisms. Compound 7 g showed a good inhibitory ef-
EXPERIMENTAL
The melting points were taken on an X-4 microscopic