10.1002/cmdc.202100153
ChemMedChem
FULL PAPER
NH (E)),7.88 (d, J = 7.6 Hz, 0.62 H (E)), 7.61 (d, J = 7.6 Hz, 0.38
H (Z)), 7.44-7.30 (m, 2 H), 7.27-7.18 (m, 2 H), 7.11 (d, J = 7.6
Hz, 1H), 6.98-6.89 (m, 4 H),6.59-6.52 (m, 1 H), 5.33 (br s, 2H,
NH2), 4.30 (br s, 2 H, CH2); 13C NMR (75 MHz), δ (ppm, DMSO-
d6): instable in DMSO; LC-MS (ESI) m/z Calculated: 505.08,
Found: 506.18; [M+H]+, tR =3.10 min (E) and 3.30 min (Z);
HPLC: C18 column: tR = 31.43 min (E) and 32.56 min (Z), purity >
99%; Melting point: > 300 °C.
1-(2-Aminophenyl)-5-(4-fluorophenyl)-N'-(2-oxoindolin-3-
ylidene)-1H-1,2,3-triazole-4-carbohydrazide 41. Yield: 61%;
yellow solid. 1H NMR (300 MHz), δ (ppm, DMSO-d6): 100% Z
form, 14.36 (br s, 1 H, NH), 11.33 (br s, 1 H, NH), 7.57 (d, J= 7,4
form, 14.34 (br s, 1 H, NH), 11.31 (br s, 1 H, NH), 7.59 (d, J =
7.4 Hz, 1 H), 7.40 (td, J = 7.8, 1.1 Hz, 1 H), 7.18 (td, J = 7.8, 1.1
Hz, 1 H), 7.12 (d, J = 8.6 Hz, 2 H), 7.15-7.09 (m, 1 H), 7.00-6.92
(m, 2 H), 6.80 (dd, J = 8.2, 0.9 Hz, 1 H), 6.55 (td, J = 7.8, 1.1 Hz,
1 H), 6.45 (d, J = 8.6 Hz, 2 H), 5.49 (br s, 2 H, NH2), 5.27 (br s, 2
H, NH2); 13C NMR (75 MHz), δ (ppm, DMSO-d6): 100% Z form,
163.1 (CO), 157.5 (CO), 150.6 (Cquat), 145.4 (Cquat), 143.2 (Cquat),
142.8 (Cquat), 137.7 (Cquat), 135.8 (Cquat), 132.1 (CH), 131.5 (2
CH), 131.4 (CH), 128.9 (CH), 123.1 (CH), 121.2 (CH), 120.7
(Cquat), 120.5 (Cquat), 116.3 (CH), 115.9 (CH), 113.1 (2 CH),
111.6 (CH), 111.4 (Cquat); LC-MS (ESI) m/z Calculated: 438.16,
Found: 439.25; [M+H]+, tR = 2.50 min; HPLC: C18 column: tR =
Hz, 1 H,), 7.50 (t, J= 8.7 Hz, 2 H), 7.37 (t, J= 7.7 Hz, 1 H), 7.22 (t, 23.49 min, purity > 99%; Melting point: > 300 °C.
J= 7.5 Hz, 2 H), 7.16 (t, J= 6.6 Hz,1 H), 7.11 (t, J= 9.3 Hz, 1 H),
7.07 (d, J= 6.6 Hz, 1 H), 6.96 (d, J= 7.8 Hz, 1 H), 6.73 (d, J= 7.7
Hz, 1 H), 6.51 (t, J= 7.1 Hz, 1 H) 5.36 (br s, 2 H, NH2); 13C NMR
1-(2-Aminophenyl)-N'-(2-oxoindolin-3-ylidene)-5-phenyl-1H-
1
1,2,3-triazole-4-carbohydrazide 45. Yield: 57%; yellow solid. H
NMR (300 MHz), δ (ppm, DMSO-d6): 100% Z form, 14.29 (br s,
1 H, NH), 11.34 (br s, 1 H, NH), 7.57 (d, J = 7.5 Hz, 1 H), 7.47
(dd, J = 7.7, 1.7 Hz, 2 H), 7.42-7.33 (m, 4 H), 7.20-7.07 (m, 2 H),
7.04 (dd, J = 7.8, 1.4 Hz, 1 H), 6.97 (d, J = 7.8 Hz, 1 H), 6.76 (dd,
J = 8.2, 0.8 Hz, 1 H), 6.52 (td, J = 7.0, 0.9 Hz, 1 H), 5.37 (br s, 2
H, NH2); 13C NMR (75 MHz), δ (ppm, DMSO-d6): 100% Z form,
163.1 (CO), 157.2 (CO), 145.4 (Cquat), 143.0 (Cquat), 142.4 (Cquat),
138.2 (Cquat), 137.1 (Cquat), 132.2 (CH), 131.6 (CH), 130.4 (2 CH),
130.1 (Cquat), 129.1 (CH), 128.2 (2 CH), 125.7 (CH), 123.1 (CH),
121.3 (CH), 120.4 (Cquat), 119.9 (Cquat), 116.2 (CH), 115.7 (CH),
111.6 (CH); LC-MS (ESI) m/z Calculated: 423.14, Found:
424.16; [M+H]+, tR = 2.78 min; HPLC: C18 column: tR = 29.06 min,
purity > 99%; Melting point: > 300 °C.
(75 MHz), δ (ppm, DMSO-d6): 100% Z form, 163.3 (Cquat, JC-F
=
245.2 Hz), 163.1 (CO), 157.2 (CO), 145.4 (CH), 143.0 (Cquat),
141.5 (Cquat), 138.3 (Cquat), 137.3 (Cquat), 133.0 (2 CH, JC-F = 8.9
Hz), 132.3 (CH), 131.7 (CH), 129.1 (CH), 123.1 (CH),122.2
(Cquat, JC-F = 3.3 Hz), 121.4 (CH), 120.4 (Cquat), 119.7 (Cquat),
116.3 (CH), 115.7 (Cquat), 115.3 (2 CH, JC-F = 22.0 Hz), 111.6
(CH); LC-MS (ESI) m/z Calculated: 441.13, Found: 442.08;
[M+H]+, tR = 2.73 min; HPLC: C18 column: tR = 29.84 min, purity >
99%; Melting point: > 300 °C.
1-(2-Aminophenyl)-N'-(2-oxoindolin-3-ylidene)-5-(4-
(trifluoromethyl)phenyl)-1H-1,2,3-triazole-4-carbohydrazide 42.
Yield: 35%; yellow solid. 1H NMR (300 MHz), δ (ppm, DMSO-d6):
100% Z form, 14.38 (br s, 1 H, NH), 11.34 (br s, 1 H, NH), 7.77
(d, J= 8.2 Hz, 2 H), 7.69 (d, J= 8.2 Hz, 2 H), 7.56 (d, J= 7.4 Hz, 1
H), 7.40 (t, J= 7.7 Hz, 1 H), 7.13-7.09 (m, 3 H), 6.96 (d, J= 8.0
Hz, 1 H), 6.73 (d, J= 7.4 Hz, 1 H), 6.54 (t, J= 7.2 Hz, 1 H), 5.40
(br s, 2 H, NH2); 13C NMR (75 MHz), δ (ppm, DMSO-d6): 100% Z
form, 163.2 (CO), 157.1 (CO), 145.3 (Cquat), 143.1 (Cquat), 141.0
(Cquat), 138.5 (Cquat), 137.8 (Cquat), 132.3 (CH), 131.9 (CH), 131.4
(2 CH), 130.3 (Cquat, JC-F= 30.0 Hz), 130.2 (Cquat), 129.11 (CH),
125.2 (2 CH, JC-F= 3.0 Hz), 124.3 (CF3, J = 270.0 Hz), 123.2
(CH), 121.4 (CH), 120.4 (Cquat), 119.5 (Cquat), 116.3 (CH), 115.8
(CH), 111.7 (CH); LC-MS (ESI) m/z Calculated: 491.13, Found:
1-(2-Aminophenyl)-N'-(2-oxoindolin-3-ylidene)-5-propyl-1H-1,2,3-
1
triazole-4-carbohydrazide 46. Yield: 23%; yellow solid. H NMR
(300 MHz), δ (ppm, DMSO-d6): 100% Z form, 14.26 (br s, 1 H),
11.32 (br s, 1 H), 7.61 (d, J = 7.0 Hz, 1 H), 7.41 (td, J = 7.7, 1.3
Hz, 1 H), 7.30 (ddd, J = 8.6, 7.3, 1.5 Hz, 1 H), 7.19-7.09 (m, J =
7.6, 5.6, 1.2 Hz, 2 H), 6.97 (d, J = 7.8 Hz, 1 H), 6.90 (dd, J = 8.3,
1.1 Hz, 1 H), 6.69 (ddd, J = 8.6, 7.6, 1.3 Hz, 1 H), 5.30 (br s, 2 H,
NH2), 2.83 (t, J = 7.9 Hz, 2 H, CH2), 1.64-1.37 (m, 2 H, CH2),
0.77 (t, J = 7.4 Hz, 3 H, CH3); 13C NMR (75 MHz), δ (ppm,
DMSO-d6): 100% Z form, 163.1 (CO), 157.9 (CO), 145.1 (Cquat),
144.2 (Cquat), 143.0 (Cquat), 138.1 (Cquat), 136.8 (Cquat), 132.2
492.07; [M+H]+, tR = 3.10 min; HPLC: C18 column: tR = 31.32 min, (CH), 131.9 (CH), 128.6 (CH), 123.1 (CH), 121.3 (CH), 120.5
purity > 99%; Melting point: > 300 °C.
(Cquat), 119.5 (Cquat), 116.59 (CH), 116.1 (CH), 111.6 (CH), 24.9
(CH2), 21.3 (CH2), 13.9 (CH3); LC-MS (ESI) m/z Calculated:
389.16, Found: 390.13; [M+H]+, tR = 2.86 min; HPLC: C18
column: tR = 30.42 min, purity > 99%; Melting point: > 300 °C.
1-(4-Aminophenyl)-5-(3,4-dichlorophenyl)-N'-(2-oxoindolin-3-
ylidene)-1H-1,2,3-triazole-4-carbohydrazide 47. Yield: 47%;
1-(2-Aminophenyl)-5-(4-methoxyphenyl)-N'-(2-oxoindolin-3-
ylidene)-1H-1,2,3-triazole-4-carbohydrazide 43. Yield: 66%;
yellow solid. 1H NMR (300 MHz), δ (ppm, DMSO-d6): 100% Z
form, 14.37 (br s, 1 H, NH), 11.33 (br s, 1 H, NH), 7.58 (d, J =
7.2 Hz, 1 H), 7.41 (d, J = 8.9 Hz, 2 H), 7.47-7.36 (m, 1 H), 7.18
(td, J = 7.7, 1.6 Hz, 1 H), 7.12 (td, J = 7.6, 0.9 Hz, 1 H), 7.04 (dd,
J = 7.9, 1.4 Hz, 1 H), 6.97 (d, J = 7.8 Hz, 1 H), 6.92 (d, J = 8.9
Hz, 2 H), 6.78 (dd, J = 8.2, 1.0 Hz, 1 H), 6.55 (td, J = 6.9, 1.2 Hz,
1 H), 5.34 (br s, 2 H, NH2), 3.76 (s, 3 H, OCH3); 13C NMR (75
MHz), δ (ppm, DMSO-d6): 100% Z form, 163.1 (CO), 160.6
(Cquat), 157.3 (CO), 145.4 (Cquat), 142.9 (Cquat), 142.2 (Cquat),
1
yellow solid. H NMR (300 MHz), δ (ppm, DMSO-d6): 100% Z
form, 14.31 (br s, 1 H, NH) 11.34 (br s, 1 H, NH), 7.82 (d, J = 2.0
Hz, 1 H), 7.69 (d, J = 8.4 Hz, 1 H), 7.56 (d, J = 7.2 Hz, 1 H), 7.40
(td, J = 7.8, 1.1 Hz, 1 H), 7.34 (dd, J = 8.4, 2.0 Hz, 1 H), 7.11 (td,
J = 7.8, 1.1 Hz, 1 H), 7.07 (d, J = 8.7 Hz, 2 H), 6.97 (d, J = 7.8
Hz, 1 H), 6.58 (d, J = 8.8 Hz, 2 H), 5.63 (br s, 2 H, NH2); 13C
138.0 (Cquat), 136.7 (Cquat), 132.1 (CH), 132.0 (2 CH), 131.5 (CH), NMR (75 MHz), δ (ppm, DMSO-d6): 100% Z form, 163.1 (CO),
129.1 (CH), 123.1 (CH), 121.3 (CH), 120.5 (Cquat), 120.1 (Cquat),
117.5 (Cquat), 116.2 (CH), 115.8 (CH), 113.7 (2 CH), 111.6 (CH),
55.6 (OCH3); LC-MS (ESI) m/z Calculated: 453.15, Found:
157.0 (CO), 150.9 (Cquat), 143.1 (Cquat), 138.7 (Cquat), 138.5
(Cquat), 137.5 (Cquat), 133.2 (CH), 133.1 (Cquat), 132.4 (CH), 131.2
(Cquat), 131.1 (CH), 130.7 (CH), 127.4 (2 CH), 126.8 (Cquat),
454.12; [M+H]+, tR = 2.80 min; HPLC: C18 column: tR = 28.82 min, 123.3 (Cquat), 123.2 (CH), 121.4 (CH), 120.4 (Cquat), 113.8 (2 CH),
purity > 99%; Melting point: > 300 °C.
111.6 (CH); LC-MS (ESI) m/z Calculated: 491.07, Found:
492.17; [M+H]+, tR = 2.99 min; HPLC: C18 column: tR = 29.23 min,
purity > 99%; Melting point: > 300 °C.
1-(2-Aminophenyl)-5-(4-aminophenyl)-N'-(2-oxoindolin-3-
ylidene)-1H-1,2,3-triazole-4-carbohydrazide 44. Yield: 57%;
yellow solid. 1H NMR (300 MHz), δ (ppm, DMSO-d6): 100% Z
14
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