732
Medicinal Chemistry Research (2021) 30:729–742
2
-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(3-chlorophenyl)
for C H BrN O S: C, 36.49; H, 2.76; N, 17.02. Found: C,
1
0
9
4
2
acetamide (7f)
36.53; H, 2.65; N, 17.23%.
Yield: 82%; mp: 177–179 °C; IR (KBr): 3358, 3324, 3045,
2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-methylpyridin-
2-yl)acetamide (7j)
−
1
1
2
996, 1678, 1625, 1608 cm ; H NMR (DMSO-d6,
5
00 MHz) δ (ppm): 10.45 (s, 1H, NH), 7.79 (s, H, H ), 7.41
2
(
2
d, J = 8 Hz, 1H, H ), 7.35 (t, J = 8 Hz, 1H, H ), 7.31 (s,
Yield: 86%; mp: 200–202 °C; IR (KBr): 3345, 3318, 3031,
4
5
1
3
−1
1
H, NH ), 7.13 (d, J = 8, H ), 3.99 (s, 2H, CH ) ppm;
C
2995, 1678, 1624, 1606 cm ; H NMR (DMSO-d6,
500 MHz) δ (ppm): 10.62 (s, 1H, NH), 8.15 (d, J = 2.5 Hz,
1H, H ), 7.93 (d, J = 8.5 Hz, 1H, H ), 7.61 (dd, J = 8.5 Hz,
2
6
2
NMR (DMSO-d , 125 MHz) δ (ppm): 170.5, 166.7, 159.2,
1
mass spectra (M ) at m/z 300.78; Anal. Calcd. for
C H ClN OS C, 39.93; H, 3.02; N, 18.63. Found: C,
6
49.6, 140.6, 133.6, 131.0, 123.8, 119.0, 118.0, 39.1 ppm;
3
6
+
J = 2.5 Hz, 1H, H ), 7.31 (s, 2H, NH ), 4.03 (s, 2H, CH ),
5 2 2
1
3
2.24 (s, 3H, CH3); C NMR (DMSO-d , 125 MHz) δ
1
0
9
4
2
6
4
0.32; H, 3.45; N, 18.98%.
(ppm): 170.5, 166.9, 159.2, 149.9, 149.8, 148.2, 139.0,
+
129.1, 113.4, 39.0, 17.7 ppm; mass spectra (M ) at m/z
2
-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(3,4-
281.04; Anal. Calcd. for C H N OS : C, 42.69; H, 3.94;
10 11 5 2
dimethoxyphenyl)acetamide (7g)
N, 24.89. Found: C, 42.81; H, 2.93; N, 24.76%.
Yield: 82%; mp: 194–196 °C; IR (KBr): 3350, 3318, 3052,
2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(5-chloropyridin-2-
yl)acetamide (7k)
−
1
1
2
5
7
994, 1689, 1618, 1604 cm ; H NMR (DMSO-d6,
00 MHz) δ (ppm): 10.11 (s, 1H, NH), 7.30 (s, 2H, NH2),
.26 (d, J = 8.7 Hz, 1H, H ), 7.06 (dd, J = 7.5, 1.0 Hz, 1H,
Yield: 88%; mp: 187–189 °C; IR (KBr): 3348, 3314, 3028,
2
−
1
1
H ), 6.89 (d, J = 8.7 Hz, 1H, H ), 3.95 (s, 2H, CH ), 3.72 (s,
2979, 1690, 1616, 1602 cm ; H NMR (DMSO-d6,
500 MHz) δ (ppm): 10.92 (s, 1H, NH), 8.39 (d, J = 2.6 Hz,
1H, H ), 8.08 (d, J = 8.9 Hz, 1H, H ), 7.92 (dd, J = 8.9,
6
5
2
13
3
1
1
3
H, OMe), 3.71 (s, 3H, OMe) ppm; C NMR (DMSO-d6,
25 MHz) δ (ppm): 170.6, 165.7, 159.4, 149.9, 149, 145.5,
32.8, 112.5, 11.1, 104.8, 104.7, 56.2, 56.1, 55.9, 55.8,
3
6
J = 2.6 Hz, 1H, H ), 7.31 (s, 2H, NH ), 4.06 (s, 2H, CH );
5
2
2
+
13
9.3, 39.2, 40.0 ppm; mass spectra (M ) at m/z 326.39;
C NMR (DMSO-d , 125 MHz) δ (ppm): 170.5, 167.4,
6
Anal. Calcd. for C H N O S : C, 44.16; H, 4.32; N,
150.8, 149.6, 146.9, 138.5, 125.8, 114.9, 39.9, 39.7,
38.9 ppm; mass spectra (M ) at m/z 301.77; Anal. Calcd.
12
14
4
3 2
+
1
7.17. Found: C, 44.36; H, 4.27; N, 17.32%.
for C H ClN OS : C, 35.82; H, 2.67; N, 23.21 Found: C,
9
8
5
2
2
-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(2,5-
36.24; H, 2.19; N, 22.89%.
dichlorophenyl)acetamide (7h)
2-((5-amino-1,3,4-thiadiazol-2-yl)thio)-N-(3,4-
Yield: 86%; mp: 194–196 °C; IR (KBr): 3354, 3322, 3028,
dimethoxyphenethyl)acetamide (7l)
−
1
1
2
5
1
975, 1687, 1628, 1611 cm ; H NMR (DMSO-d6,
00 MHz) δ (ppm): 9.94 (s, 1H, NH), 7.95 (d, J = 2.5 Hz,
H, H ), 7.54 (d, J = 8.5 Hz, H ), 7.34 (s, 2H, NH ), 7.27
Yield: 88%; mp: 187–189 °C; IR (KBr): 3348, 3314, 3028,
−
1
1
2979, 1694, 1626, 1612 cm ; H NMR (DMSO-d6,
500 MHz) δ (ppm): 8.37 (t, J = 5.5 Hz, 1H, NH), 7.36 (s,
2H, NH ), 6.83 (d, J = 8.15 Hz, 1H, H ), 6.80 (s, 1H, H ),
2
3
2
1
3
(
dd, J = 8.5 Hz, J = 2.5 Hz, 1H, H ), 4.09 (s, 1H, CH ); C
4 2
NMR (DMSO-d , 125 MHz) δ (ppm): 170.6, 167.5, 159.2,
6
2
5
2
1
3
49.6, 136.3, 132.1, 131.4, 126.2, 124.4, 124.3, 39.7, 38.6,
8.5 ppm; mass spectra (M ) at m/z 333.95; Anal. Calcd.
6.69 (d, J = 8.15, 1H, H ), 3.73 (s, 3H, OCH ), 3.70 (s, 3H,
6 3
+
OCH ), 3.64(s, 2H, CH -S), 3.25 (t, J = 6.75, 2H, CH2-
3 2
1
3
for C H Cl N OS : C, 35.83; H, 2.41; N, 16.71. Found: C,
NH), 2.63 (t, J = 6.75, 2H, CH -phe); C NMR (DMSO-
1
0
8
2
4
2
2
3
6.17; H, 2.63; N, 16.64%.
d6, 125 MHz) δ (ppm): 169.1, 167.2, 164.0, 150.1, 149.0,
1
47.6, 132.2, 120.9, 112.9, 112.3, 55.8, 41.3, 39.7,
+
2
-((5-amino-1,3,4-oxadiazol-2-yl)thio)-N-(4-bromophenyl)
35.0 ppm; mass spectra (M ) at m/z 354.44; Anal. Calcd.
acetamide (7i)
for C H N O S : C, 47.44; H, 5.12; N, 15.81 Found: C,
1
4
18
4
3 2
47.24; H, 5.33; N, 15.63%.
Yield: 78%; mp: 190–192 °C; IR (KBr): 3350, 3316, 3015,
−
1
1
2
5
2
3
988, 1685, 1619, 1600 cm ; H NMR (DMSO-d6,
00 MHz) δ (ppm): 10.39 (s, 1H, NH), 7.55 (d, J = 9 Hz,
H, H3, 5), 7.50 (d, J = 9 Hz, 2H, H1, 6), 7.29 (s, 2H, NH2),
Urease inhibitory activity evaluation
The urease inhibitory activity of the test and inhibitor
compounds was evaluated based on the Berthelot colori-
13
.99 (s, 2H, CH ) ppm; C NMR (DMSO-d6, 125 MHz) δ
2
(
3
ppm): 170.5, 166.5, 149.7, 138.6, 132.1, 121.6, 115.6,
9.2 ppm; mass spectra (M ) at m/z 329.17; Anal. Calcd.
metric method. In this method, the reaction of ammonia
+
−
(NH ), hypochlorite (OCl ), and phenol will make a
3