DARU J Pharm Sci
Fig. 1 Chemical structures of
some compounds with α-
glucosidase inhibitory and anti-
hyperglycemia activity
(100). Anal. Calcd. For C20H14Cl2N2O: C, 65.06; H, 3.82; N,
7.59. Found: C, 65.26; H, 3.61; N, 7.44.
7.05(t, 2H, J = 8.0 Hz), 7.15(d, J = 8.5 Hz, 2H), 7.27(d, J =
8.5 Hz, 2H), 7.46(d, J = 8.0 Hz, 2H), 7.56–7.60(m, 2H).
13CNMR (CdCl3) δ: 165.0, 163.0, 154.1, 139.5, 138.3,
131.4, 130.1, 130.0, 130.0, 129.4, 128.9, 127.1, 125.5,
121.2, 116.2, 116.0, 100.4, 21.4. Mass (M/z, (%)); 366 (25),
246(100, 212 (29), 95 (18), 69 (35). Anal. Calcd. For
C21H16ClFN2O: C, 68.76; H, 4.40; N, 7.64. Found: C,
68.39; H, 3.99; N, 7.78.
3-(4-chlorophenyl)-4-(4-fluorophenyl)
-5-phenyl-4,5-dihydro-1,2,4-oxadiazole (6d)
Yield: 78%. Mp: 143-145 °C. 1HNMR (CdCl3) δ; 6.45(s, 1H,
H5-oxadiazole), 6.78–6.82(m, 2H), 6.88–6.92(t, 2H, J = 9.0),
7.32(d, J = 8.5 Hz, 2H), 7.45–7.48(m, 3H), 7.52(d, J = 8.5 Hz,
2H), 7.55–7.60(m, 2H). 13CNMR (CdCl3) δ; 161.7, 154.6,
138.3, 137.0, 136.7, 130.00, 129.6, 129.2, 129.0, 128.9,
127.3, 126.8, 126.8, 123.6, 116.4, 116.3, 101.0. Mass (M/z,
(%)); 352 (25), 289 (19), 246 (100), 198 (27), 153 (21). Anal.
Calcd. For C20H14ClFN2O: C, 68.09; H, 4.00; N, 7.94. Found:
C, 68.31; H, 3.91; N, 7.67.
3-(4-chlorophenyl)-4-(4-fluorophenyl)-5-(p-tolyl)
-4,5-dihydro-1,2,4-oxadiazole (6 g)
Yield: 65%. Mp: 125-128 °C. 1HNMR (CdCl3) δ; 2.38(s, 3H,
CH3), 6.42(s, 1H, H5-oxadiazole), 6.72–6.808(m, 2H), 6.89(t,
J = 7.1 Hz), 2H), 7.26(d, J = 8.0 Hz, 2H), 7.33(d, J = 8.5 Hz,
2H), 7.45(d, J = 8.0 Hz, 2H), 7.51(d, J = 8.5 Hz, 2H).13CNMR
(CdCl3) δ; 161.6, 159.7, 154.6, 140.1, 136.9, 136.6, 135.3,
129.6, 129.2, 129.0, 127.3, 126.8, 126.7, 123.7, 116.4,
116.2, 101.0, 21.4. Mass (M/z, (%)); 366 (18), 246(100),
213 (32), 95 (27), 69 (34). Anal. Calcd. For C21H16ClFN2O:
C, 68.76; H, 4.40; N, 7.64. Found: C, 68.46; H, 4.19; N, 7.39.
3,4-bis(4-chlorophenyl)-5-(p-tolyl)
-4,5-dihydro-1,2,4-oxadiazole (6e)
Yield: 86%. Mp: 120-122 °C. 1HNMR (CdCl3) δ; 2.41(s, 3H,
CH3), 6.46(s, 1H, H5-oxadiazole), 6.72(d, J = 8.5 Hz, 2H),
7.16(d, J = 8.5 Hz, 2H), 7.26(d, J = 8.0 Hz, 2H), 7.34(d, J =
8.0 Hz, 2H), 7.45(d, J = 8.0 Hz, 2H), 7.52(d, J = 8.0 Hz, 2H).
13CNMR (CdCl3) δ; 154.1, 140.1, 139.4, 136.8, 135.3, 131.4,
129.6, 129.4, 129.2, 129.1, 127.1, 125.5, 123.6, 100.5, 21.4.
Mass (M/z, (%)); 382 (33), 262(100), 229 (34), 192 (11), 125
(17), 91 (18). Anal. Calcd. For C21H16Cl2N2O: C, 65.81; H,
4.21; N, 7.31. Found: C, 65.66; H, 4.09; N, 7.25.
3-(4-chlorophenyl)-5-(4-methoxyphenyl)
-4-phenyl-4,5-dihydro-1,2,4-oxadiazole (6 h)
Yield: 72%. Mp: 119-122 °C. 1HNMR (CdCl3) δ; 3.85(s, 3H,
OCH3), 6.49(s, 1H, H5-oxadiazole), 6.79(d, J = 7.5 Hz, 2H),
6.96 (d, J = 8.0 Hz, 2H), 7.13(m, 1H), 7.19(t, J = 7.5 Hz, 2H),
7.31(d, J = 8.0 Hz, 2H), 7.50–7.56(m, 4H). 13CNMR (CdCl3)
δ; 160.83, 154.36, 140.86, 136.49, 130.80, 129.30, 129.23,
128.97, 128.70, 125.86, 124.44, 124.06, 114.21, 100.52,
55.35. Mass (M/z, (%)); 364 (36), 228 (100), 216 (41), 1135
(29), 77 (39). Anal. Calcd. For C21H17ClN2O2: C, 69.14; H,
4.70; N, 7.68. Found: C, 69.26; H, 4.55; N, 7.54.
4-(4-chlorophenyl)-3-(4-fluorophenyl)-5-(p-tolyl)
-4,5-dihydro-1,2,4-oxadiazole (6f)
1
Yield: 86%. Mp: 80-82 °C. HNMR (CdCl3) δ; 2.43(s, 3H,
CH3), 6.46(s, 1H, H5-oxadiazole), 6.72(d, J = 8.5 Hz, 2H),