JOURNAL OF CHEMICAL RESEARCH 2016 271
1
3
3
7
8
098, 2925, 2854, 1610, 1533, 1493, 1483, 1462, 1350, 1040, 810, 750,
6.54–6.55 (d, J = 4.0 Hz, 1H, CH–H), 5.55 (s, 1H, CH –H); C NMR
2
1
38; H NMR (400 MHz, CDCl ): δ 8.47 (d, J = 4.0 Hz, 1H, ArH),
(100 MHz, CDCl ): δ 144.6, 135.9, 134.5, 133.1, 130.6, 128.9, 128.8, 127.8,
127.3, 126.2, 125.9, 124.6, 121.9, 121.1, 119.8, 109.5, 102.2, 41.9; ESI-MS:
343 [M + 1] ; HRMS calcd for C H F N Na: [M + Na] : 365.0985; found:
3
3
.23–8.26 (m, 1H, ArH), 8.03 (d, J = 8.0 Hz, 1H, CH–H), 7.64–7.68
+
+
(m, 3H, ArH), 7.40 (d, J = 8.0 Hz, 1H, ArH), 7.20–7.25 (m, 2H, ArH),
18 13 3 4
7
2
.13 (d, J = 8.0 Hz, 16.0 Hz, 1H, CH–H), 6.57 (s, 1H, CH–H), 5.55 (s,
365.0980.
1-{[1-(2-Fluorophenyl)-1,2,3-triazol-4-yl]methyl}-1H-indole
13
H, CH –H); C NMR (100 MHz, CDCl ): δ 148.9, 145.5, 137.5, 136.0,
(3l):
2
3
–1
131.9, 129.1, 128.7, 126.4, 123.6, 122.6, 121.6, 120.9, 119.6, 115.1, 110.5,
White solid; yield 84%; m.p. 88–89.7 °C; IR (KBr) (ν cm ): 3129, 3083,
+
101.6, 41.1; ESI-MS: 320 [M + 1] ; HRMS calcd for C H N O Na: [M
3025, 1672, 1611, 1597, 1555, 1512, 1483, 1474, 1462, 1425, 1395, 1240,
1
7
13
5
2
+
1
+
Na] : 342.0961; found: 342.0966.
-{[1-(4-Nitrophenyl)-1,2,3-triazol-4-yl]methyl}-1H-indole
1049, 758, 744, 719; H NMR (400 MHz, DMSO-d ): δ 8.61 (s, 1H, CH–
6
1
(3f):
White solid; yield 85%; m.p. 162–163 °C; IR (KBr) (ν cm ): 3132,
087, 2939, 2855, 1616, 1598, 1521, 1484, 1462, 1434, 1398, 1345, 829,
H), 7.66 (d, J = 8.0 Hz, 1H, ArH), 7.51–7.59 (m, 4H, ArH), 7.41 (t, J = 8.0
–
1
Hz, 16.0 Hz, 1H, ArH), 7.15 (t, J = 4.0 Hz, 16.0 Hz, 1H, CH–H), 7.03 (t,
13
3
J = 4.0 Hz, 16.0 Hz, 1H, CH–H), 5.57 (s, 2H, CH –H); C NMR (100
2
1
7
48, 718; H NMR (400 MHz, CDCl ): δ 8.33 (d, J = 8.0 Hz, 2H, ArH),
MHz, DMSO-d ): δ 155.3, 152.9, 144.6, 136.0, 131.7, 131.6, 129.1, 128.7,
3
6
7.83 (d, J = 8.0 Hz, 2H, ArH), 7.65 (t, J = 8.0 Hz, 16.0 Hz, 2H, ArH),
126.2, 121.6, 120.9, 119.6, 117.6, 117.4, 110.5, 101.6, 40.9; ESI-MS: 293 [M
+
+:
7.39 (d, J = 8.0 Hz, 1H, ArH), 7.20–7.24 (m, 2H, ArH), 7.14 (t, J = 4.0
+ 1] ; HRMS calcd for C H FN Na: [M + Na] 315.1016; found: 315.1014.
17 13 4
Hz, 16.0 Hz, 1H, CH–H), 6.58 (d, J = 4.0 Hz, 1H, CH –H), 5.55 (s,
1-{[1-(2-Chlorophenyl)-1,2,3-triazol-4-yl]methyl}-1H-indole
(3m):
2
13
–1
2
1
H, CH –H); C NMR (100 MHz, CDCl ): δ 147.1, 146.4, 140.8, 135.8,
White solid; Yield 82%; m.p. 79–80 °C; IR (KBr) (ν cm ): 3148, 3055,
2
3
28.8, 127.8, 125.4, 122.1, 121.2, 120.3, 112.0, 119.8, 109.4, 102.5, 41.9;
2949, 2854, 1696, 1611, 1591, 1582, 1552, 1512, 1493, 1461, 1433, 1376,
+
+
1
ESI-MS: 320 [M + 1] ; HRMS calcd for C H N O Na: [M + Na] :
1309, 776, 758, 745, 718, 690; H NMR (400 MHz, DMSO-d ): δ 8.58 (s,
17
13
5
2
6
3
42.0961; found: 342.0957.
-{[1-(2-Methyl-5-nitrophenyl)-1,2,3-triazol-4-yl]methyl}-1H-
indole (3g): White solid; yield 85%; m.p. 115–117 °C; IR (KBr)
1H, CH–H), 7.74 (d, J = 8.0 Hz, 1H, ArH), 7.52–7.66 (m, 5H, ArH), 7.50
(d, J = 4.0 Hz, 1H, CH–H), 7.15 (t, J = 4.0 Hz, 8.0 Hz, 1H, ArH), 7.03 (d,
J = 8.0 Hz, 16.0 Hz, 1H, ArH), 6.47 (d, J = 4.0 Hz, 1H, CH–H); C NMR
1
13
–1
(
1
ν cm ): 3150, 3094, 3057, 2940, 1612, 1521, 1485, 1462, 1441, 1376,
347, 823, 796, 738, 652; H NMR (400 MHz, CDCl ): δ 8.21–8.23 (m,
(100 MHz, DMSO-d ): δ 144.0, 136.1, 134.8, 132.0, 131.0, 129.1, 128.8,
6
1
128.8, 128.8, 126.1, 121.6, 120.9, 119.6, 110.6, 101.6, 41.0; ESI-MS: 310
3
+
1H, ArH), 8.13 (d, J = 4.0 Hz, 1H, ArH), 7.64 (d, J = 8.0 Hz, 1H, =CH–
[M + 1]; HRMS calcd for C H ClN Na: [M +Na] : 331.0721; found:
17
13
4
H), 7.51 (d, J = 8.0 Hz, 1H, ArH), 7.40 (t, J = 4.0 Hz, 8.0 Hz, 2H, ArH),
.20–7.25 (m, 2H, ArH), 7.12 (t, J = 8.0 Hz, 16.0 Hz, 1H, =CH–H), 5.56
331.0725.
1-{[1-(3-Chlorophenyl)-1,2,3-triazol-4-yl]methyl}-1H-indole
7
(3n):
13
–1
(
s, 1H, =CH–H), 5.57 (s, 2H, CH –H), 2.27 (s, 3H, CH –H); C NMR
White solid; yield 93%; m.p. 104–106 °C; IR (KBr) (ν cm ): 3142, 3098,
2
3
(
1
100 MHz, CDCl ): δ 146.3, 145.3, 141.5, 136.5, 135.8, 132.5, 128.8,
2939, 2852, 1685, 1593, 1508, 1492, 1462, 1433, 1398, 798, 778, 749, 716;
3
1
27.8, 124.3, 123.3, 122.0, 121.2, 121.1, 119.8, 109.4, 102.4, 41.9, 18.5;
H NMR (400 MHz, CDCl ): δ 7.66 (d, J = 8.0 Hz, 2H, ArH, CH–H), 7.52
3
+
+
ESI-MS: 334 [M + 1] ; HRMS calcd for C H N O Na: [M + Na] :
(d, J = 8.0 Hz, 2H, ArH), 7.38–7.41 (m, 3H, ArH), 7.23 (t, J = 8.0 Hz, 16.0
18
15
5
2
3
56.1118; found: 356.1114.
Hz, 2H, ArH), 7.14 (t, J = 8.0 Hz, 16.0 Hz, 1H, CH–H), 6.58 (d, J = 4.0 Hz,
13
1-[(1-o-Tolyl-1,2,3-triazol-4-yl)methyl]-1H-indole (3h): White solid;
1H, CH–H), 5.54 (s, 2H, CH –H); C NMR (100 MHz, CDCl ): δ 145.8,
2 3
–
1
yield 86%; m.p. 82.6–83.7 °C; IR (KBr) (ν cm ): 3135, 3085, 3055, 2929,
862, 2793, 1707, 1611, 1585, 1556, 1504, 1484, 1463, 1440, 1399, 1382,
137.6, 135.8, 135.5, 130.8, 128.9, 128.8, 127.8, 122.0, 121.2, 120.6, 119.9,
+
2
119.8, 118.4, 109.4, 102.4, 42.0; ESI-MS: 310 [M + 1] ; HRMS calcd for
1
+
7
64, 741; H NMR (400 MHz, CDCl ): δ 7.63 (d, J = 8.0 Hz, 1H, CH–H),
C H ClN Na: [M + Na] : 331.0721; found: 331.0724.
3
17 13
4
7.40 (d, J = 8.0 Hz, 1H, ArH), 7.17–7.36 (m, 7H, ArH), 7.11 (t, J = 8.0
Antifungal activity
Hz, 16.0 Hz, 1H, CH–H), 6.54 (d, J = 4.0 Hz, 1H, CH–H), 6.52 (s, 2H,
1
3
The antifungal activity of the target compounds against
Colletotrichum capsici and cotton Physalospora pathogens, using
hexaconazole and flutriafol as the positive controls, was evaluated by
the College of Life Science, Henan Normal University. The procedures
were carried out as described below.
CH –H), 2.11 (s, 3H, CH –H); C NMR (100 MHz, CDCl ): δ 144.6,
2
3
3
136.2, 135.9, 133.6, 131.5, 129.9, 128.8, 127.9, 126.8, 125.9, 123.4, 121.9,
+
121.1, 119.8, 109.5, 102.2, 42.1, 17.8; ESI-MS: 289 [M + 1] ; HRMS calcd
+
for C H N Na: [M + Na] : 311.1267; found: 311.1262.
18
16
4
1-[(1-p-Tolyl-1,2,3-triazol-4-yl)methyl]-1H-indole (3i): White solid;
–
1
–
1
A stock solution of each compound was prepared at 0.2 mg mL
yield 87%; m.p. 92–94 °C; IR (KBr) (ν cm ): 3125, 3082, 3055, 2921,
864, 1612, 1549, 1518, 1485, 1466, 1445, 1397, 1381, 1354, 818, 757,
–1
using DMSO as a solvent. A working solution (0.02 mg mL ) was
then prepared by diluting the stock solution (0.1 mL) with sterilised
water (0.9 mL) in a 10 cm diameter Petri dish. Potato dextrose agar
2
1
7
40, 728; H NMR (400 MHz, CDCl ): δ 7.64 (d, J = 8.0 Hz, 1H, ArH),
3
7.51 (s, 1H, =CH–H), 7.40–7.45 (m, 3H, ArH), 7.19–7.22 (m, 4H, ArH),
(
PDA, 9 mL) was then added to prepare the plate. Before the plate
7.12 (t, J = 4.0 Hz, 8.0 Hz, 1H, =CH–H), 6.54 (s, 1H, =CH–H), 5.49
1
3
solidification, the PDA was completely mixed by turning around the
Petri dish in the sterilised operation disk six times to decentralise the
compounds in PDA evenly. Then 0.8 mm of diameter of the fungi
cake was vaccinated on the plate and cultured in the incubator at
(s, 2H, CH –H), 2.35 (s, 3H, CH –H); C NMR (100 MHz, CDCl ):
2
3
3
δ 145.3, 138.9, 135.9, 134.5, 130.2, 128.9, 127.9, 122.0, 121.2, 120.3,
+
112.0, 119.8, 109.6, 102.2, 42.0, 21.1; ESI-MS: 289 [M + 1] ; HRMS
+
calcd for C H N Na: [M + Na] : 311.1267; found: 311.1265.
18
16
4
32 °C. After 24 h, the diameter of fungi spread was measured. Growth
4
-{4-[(1H-Indol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}phenol
(3j):
–
1
inhibition was then calculated using the positive controls.
White solid; yield 84%; m.p. 172–173 °C; IR (KBr) (ν cm ): 3423,
3132, 3105, 2943, 2841, 2710, 1601, 1518, 1479, 1469, 1427, 1381, 1063,
1
8
39, 753, 665; H NMR (400 MHz, CDCl ): δ 7.65 (d, J = 8.0 Hz, 1H,
This work was supported by the Natural Science Foundation
of China (no. 21172058), the Scientific Research Foundation
for Doctors (no. 01036500508) and the key scientific and
technological project of Henan province (no. 152102310312).
3
CH–H), 7.40–7.48 (m, 4H, ArH), 7.22 (d, J = 12.0 Hz, 3H, ArH), 7.13
(t, J = 8.0 Hz, 16.0 Hz, 1H, ArH), 6.92 (d, J = 12.0 Hz, 2H, CH–H),
13
6
.56 (s, 1H, OH–H), 5.53 (s, 2H, CH –H); C NMR (100 MHz,
2
DMSO-d ): δ 158.2, 144.7, 135.9, 129.1, 129.1, 128.7, 122.4, 122.0,
6
+
121.6, 120.9, 119.6, 116.4, 110.6, 101.5, 41.1; ESI-MS: 291 [M + 1] ;
Paper 1603872 doi: 10.3184/174751916X14597828245275
Published online: 20 April 2016
+
HRMS calcd for C H N ONa: [M + Na] : 313.1065; found: 313.1060.
17
14
4
1
-({1-[2-(Trifluoromethyl)phenyl]-1,2,3-triazol-4-yl}methyl)-
1H-indole (3k): White solid; yield 91%; m.p. 84–85 °C; IR (KBr)
–1
(
1
ν cm ): 3158, 3064, 2941, 2860, 1645, 1609, 1558, 1510, 1485, 1465,
441, 1366, 1317, 770, 741; H NMR (400 MHz, CDCl ): δ 7.80 (d,
References
1
3
1
2
L. Bos, Crop Prot., 1982, 1, 263.
Z. Fan, Z. Shi, H. Zhang, X. Liu, L. Bao, X. Zuo, Q. Zheng and N. Mi, J.
Agr. Food Chem., 2009, 57, 4279.
J = 8.0 Hz, 1H, ArH), 7.62–7.69 (m, 3H, ArH), 7.40–7.44 (m, 3H, ArH),
7.20–7.25 (m, 2H, ArH), 7.12 (t, J = 8.0 Hz, 16.0 Hz, 1H, CH–H),