H. Liu, et al.
Bioorganic Chemistry 99 (2020) 103807
4.1.17. (E)-1-(4-fluorophenyl)-5-(((2-(p-tolyl)-1H-indol-3-yl)methylene)
+
2
1.1. MS (ESI): 420.15(C26
H
18FN
5
, [M + H] ). Anal. Calcd for
C
26
H
18FN
5
: C, 74.45; H, 4.33; F, 4.53; N, 16.70; Found: C, 74.43; H,
amino)-1H-pyrazole-4-carbonitrile (8I-n)
1
4
.31; F, 4.52; N, 16.71.
H NMR (600 MHz, CDCl ) δ 9.27 (s, 1H), 8.68 (s, 1H), 8.32 (d,
3
J = 7.8 Hz, 1H), 7.85 (s, 1H), 7.79 (dd, J = 8.7, 4.8 Hz, 2H), 7.60 (d,
4
.1.12. (E)-5-(((2-(4-chlorophenyl)-1H-indol-3-yl)methylene)amino)-1-
J = 7.9 Hz, 2H), 7.45 (d, J = 8.1 Hz, 1H), 7.41 (d, J = 7.8 Hz, 2H),
phenyl-1H-pyrazole-4-carbonitrile (8I-i)
7.34 (t, J = 7.6 Hz, 1H), 7.24 (d, J = 7.8 Hz, 1H), 7.17 (t, J = 8.5 Hz,
1
13
H NMR (600 MHz, CDCl
3
) δ 9.21 (s, 1H, Indole-H), 8.40 (d,
2H), 2.46 (s, 3H). C NMR (150 MHz, CDCl
3
) δ 161.2, 154.9, 148.8,
J = 7.4 Hz, 1H, CH = N), 8.35 (d, J = 7.9 Hz, 1H, Ar-H), 7.87 (s, 1H,
142.4, 140.6, 136.1, 130.2, 129.2, 126.9, 126.9, 126.3, 126.2, 125.0,
Pyrazole-H), 7.79 (d, J = 8.1 Hz, 1H, Ar-H), 7.65 – 7.60 (m, 2H, Ar-H),
124.5, 123.0, 122.8, 115.6, 115.5, 114.9, 111.2, 80.1, 21.4. MS (ESI):
+
7
.59 – 7.38 (m, 7H, Ar-H), 7.33 (t, J = 6.9 Hz, 1H, Ar-H), 7.22 (t,
420.15(C26
H18FN
5
, [M + H] ). Anal. Calcd for C26
H
18FN : C, 74.45;
5
1
3
J = 7.5 Hz, 1H, Ar-H). C NMR (150 MHz, CDCl
3
) δ 160.8 (CH = N),
H, 4.33; F, 4.53; N, 16.70; Found: C, 74.46; H, 4.32; F, 4.52; N, 16.71.
1
1
1
47.1, 142.4 (Pyrazole-C), 135.4 (Ar-C), 130.6 (Ar-C), 130.5 (Ar-C),
29.8 (Ar-C), 129.5 (Ar-C), 128.8 (Ar-C), 128.4 (Ar-C), 125.4 (Ar-C),
24.9 (Ar-C), 124.6 (Ar-C), 123.4 (Indole-C), 123.3 (Ar-C), 122.9 (Ar-
4
.1.18. (E)-1-(4-chlorophenyl)-5-(((2-(p-tolyl)-1H-indol-3-yl)methylene)
amino)-1H-pyrazole-4-carbonitrile (8I-o)
C), 122.3 (Ar-C), 121.0 (Ar-C), 111.3 (Indole-C), 111.0 (Pyrazole-C),
1
H NMR (600 MHz, CDCl ) δ 10.08 (s, 1H), 9.25 (s, 1H), 8.80 (s,
3
+
8
1.7(Pyrazole-C). MS (ESI): 422.11(C25
H16ClN
5
, [M + H] ). Anal.
1
7
8
H), 8.42 (d, J = 8.8 Hz, 1H), 8.36 (d, J = 7.7 Hz, 1H), 7.85 (s, 1H),
.80 (d, J = 8.8 Hz, 1H), 7.60 (d, J = 7.9 Hz, 1H), 7.53 (dd, J = 10.2,
.6 Hz, 1H), 7.45 (t, J = 7.7 Hz, 2H), 7.40 (d, J = 7.8 Hz, 1H), 7.35 (d,
Calcd for C25
H
16ClN : C, 71.17; H, 3.82; Cl, 8.40; N, 16.60; Found: C,
5
7
1.15; H, 3.81; Cl, 8.42; N, 16.61.
J = 7.0 Hz, 1H), 7.32 (dd, J = 6.0, 3.1 Hz, 1H), 7.27 (d, J = 7.9 Hz,
4
.1.13. (E)-5-(((2-(4-chlorophenyl)-1H-indol-3-yl)methylene)amino)-1-
1
3
1
1
1
2
H), 2.46–2.45 (d, J = 6 Hz, 3H). C NMR (150 MHz, CDCl ) δ 161.4,
3
(
4-fluorophenyl)-1H-pyrazole-4-carbonitrile (8I-j)
54.4,137.4, 136.4, 132.2, 130.2, 129.9, 129.3, 129.2, 128.8, 125.4,
1
H NMR (600 MHz, CDCl ) δ 9.23 (s, 1H), 8.78 (s, 1H), 8.32 (d,
3
24.5, 124.4, 124.3, 123.1, 122.8, 122.3, 114.8, 111.2, 110.8, 80.4,
J = 8.0 Hz, 1H), 7.86 (s, 1H), 7.78 (dd, J = 6.9, 3.8 Hz, 2H), 7.63 (d,
J = 7.2 Hz, 2H), 7.57 (d, J = 8.3 Hz, 2H), 7.46 (d, J = 8.0 Hz, 1H),
+
2.7. MS (ESI): 436.13(C26
H
18ClN
5
, [M + H] ). Anal. Calcd for
C
26
H
18ClN : C, 71.64; H, 4.16; Cl, 8.13; N, 16.07; Found: C, 71.62; H,
5
7
1
1
1
.36 (t, J = 7.5 Hz, 1H), 7.17 (t, J = 8.4 Hz, 2H), 6.99 (d, J = 21.1 Hz,
13
4
.18; Cl, 8.12; N, 16.06.
H). C NMR (150 MHz, CDCl ) δ 160.7, 146.9, 142.3, 136.6, 130.5,
3
29.8, 129.3, 128.2, 126.3, 126.3, 126.2, 126.1, 124.8, 123.2, 122.9,
15.7, 115.5, 112.3, 111.3, 80.2. MS (ESI): 440.10(C25
H
15ClFN
5
,
4.1.19. (E)-1-(p-tolyl)-5-(((2-(p-tolyl)-1H-indol-3-yl)methylene)amino)-
+
[
M + H] ). Anal. Calcd for C25
H
15ClFN
5
: C, 68.26; H, 3.44; Cl, 8.06; F,
1H-pyrazole-4-carbonitrile (8I-p)
1
4
.32; N, 15.92; Found: C, 68.24; H, 3.45; Cl, 8.08; F, 4.31; N, 15.94.
H NMR (600 MHz, CDCl ) δ 9.24 (s, 1H), 8.79 (s, 1H), 8.37 (d,
3
J = 7.9 Hz, 1H), 7.84 (s, 1H), 7.68 (d, J = 8.3 Hz, 1H), 7.62 (s, 1H),
7.59 (d, J = 8.0 Hz, 1H), 7.53 (t, J = 8.7 Hz, 1H), 7.43 (d, J = 8.1 Hz,
1H), 7.39 (d, J = 7.9 Hz, 1H), 7.36 (d, J = 8.3 Hz, 1H), 7.32 (dd,
J = 8.0, 5.7 Hz, 2H), 7.28 (s, 1H), 7.22 (t, J = 7.5 Hz, 1H), 2.44 (dd,
4
.1.14. (E)-1-(4-chlorophenyl)-5-(((2-(4-chlorophenyl)-1H-indol-3-yl)
methylene)amino)-1H-pyrazole-4-carbonitrile (8I-k)
1
H NMR (600 MHz, CDCl ) δ 10.07 (s, 1H), 8.42 (d, J = 6.0 Hz,
3
1
3
1
7
2
H), 8.36 (d, J = 8.1 Hz, 1H), 7.87 (s, 1H), 7.79 (d, J = 8.5 Hz, 1H),
J = 18.5, 3.8 Hz, 6H). C NMR (150 MHz, CDCl ) δ 161.0, 154.5,
3
.64 (d, J = 7.7 Hz, 1H), 7.58 (t, J = 9.4 Hz, 3H), 7.53 (d, J = 8.3 Hz,
151.9, 141.0, 140.5, 137.7, 136.1, 130.5, 132.6, 130.5, 130.2, 129.2,
1
3
H), 7.46 – 7.42 (m, 2H), 7.37 – 7.32 (m, 2H). C NMR (150 MHz,
129.2, 124.3, 124.2, 124.2, 123.1, 122.8, 114.0, 111.1, 104.8, 81.7,
+
CDCl
3
) δ 160.8, 147.1, 135.4, 130.6, 130.5, 129.8, 129.5, 128.8, 128.4,
21.1. MS (ESI): 416.18(C27
H
21
N
5
, [M + H] ). Anal. Calcd for
1
1
25.4, 124.9, 124.6, 123.4, 123.3, 122.9, 122.3, 121.0, 115.3 111.3,
C
27
H
21
N : C, 78.05; H, 5.09; N, 16.86; Found: C, 78.04; H, 5.08; N,
5
+
11.0, 81.7. MS (ESI): 456.07(C25
H
15Cl
2
N
5
, [M + H] ). Anal. Calcd
16.85.
for C25
H
15Cl
2
N : C, 65.80; H, 3.31; Cl, 15.54; N, 15.35; Found: C, 65.82;
5
H, 3.30; Cl, 15.52; N, 15.34.
4
.1.20. (E)-5-(((2-(4-methoxyphenyl)-1H-indol-3-yl)methylene)amino)-
1
-phenyl-1H-pyrazole-4-carbonitrile (8I-q)
4
.1.15. (E)-5-(((2-(4-chlorophenyl)-1H-indol-3-yl)methylene)amino)-1-
1
H NMR (600 MHz, CDCl ) δ 10.06 (s, 1H), 8.75 (s, 1H), 8.43 – 8.38
3
(
p-tolyl)-1H-pyrazole-4-carbonitrile (8I-l)
(
m, 1H), 7.64 (s, 1H), 7.58 (d, J = 8.7 Hz, 2H), 7.55 – 7.51 (m, 3H),
1
H NMR (600 MHz, CDCl ) δ 9.20 (s, 1H), 8.43 – 8.39 (m, 1H), 8.37
3
7
3
1
1
.50 (t, J = 4.3 Hz, 3H), 7.47 – 7.43 (m, 2H), 7.06 (d, J = 8.7 Hz, 2H),
13
(
d, J = 7.9 Hz, 1H), 7.85 (s, 1H), 7.58 (d, J = 8.3 Hz, 2H), 7.55 (d,
.89 (d, J = 6.3 Hz, 3H). C NMR (150 MHz, CDCl ) δ 162.2, 161.2,
3
J = 8.3 Hz, 1H), 7.52 (d, J = 8.3 Hz, 2H), 7.34 (dt, J = 14.3, 8.6 Hz,
51.9, 149.7, 149.0, 141.2, 137.0, 135.4, 130.8, 129.9, 128.9, 126.3,
4
H), 7.28 (s, 1H), 7.23 (d, J = 7.3 Hz, 1H), 2.42 (d, J = 4.8 Hz, 3H).
24.2, 124.1, 123.1, 122.3, 122.2, 114.7, 113.9, 110.8, 80.4, 55.4. MS
1
3
C NMR (150 MHz, CDCl ) δ 160.5, 142.1, 141.0, 139.2, 136.4, 130.7,
3
+
(
ESI): 418.16(C26
H
19
N
5
O, [M + H] ). Anal. Calcd for C26
H
19
N O: C,
5
1
1
30.5, 130.5, 129.7, 129.4, 129.2, 124.6, 124.6, 124.2, 123.3, 123.1,
7
3
4.80; H, 4.59; N, 16.78; O, 3.83; Found: C, 74.82; H, 4.58; N, 16.76; O,
.82.
23.0, 122.3, 111.2, 111.0, 80.7, 21.1. MS (ESI): 436.13(C26
H
18ClN ,
5
+
[
M + H] ). Anal. Calcd for C26
H
18ClN : C, 71.64; H, 4.16; Cl, 8.13; N,
5
1
6.07; Found: C, 71.65; H, 4.18; Cl, 8.12; N, 16.06.
4
.1.21. (E)-1-(4-fluorophenyl)-5-(((2-(4-methoxyphenyl)-1H-indol-3-yl)
4
.1.16. (E)-1-phenyl-5-(((2-(p-tolyl)-1H-indol-3-yl)methylene)amino)-
methylene)amino)-1H-pyrazole-4-carbonitrile (8I-r)
1
1
H-pyrazole-4-carbonitrile (8I-m)
H NMR (600 MHz, CDCl ) δ 9.25 (s, 1H), 8.69 (s, 1H), 8.31 (d,
3
1
H NMR (600 MHz, CDCl
3
) δ 9.27 (s, 1H), 8.64 (s, 1H), 8.37 (d,
J = 7.9 Hz, 1H), 7.85 (s, 1H), 7.79 (dd, J = 8.7, 4.8 Hz, 2H), 7.64 (d,
J = 8.5 Hz, 2H), 7.44 (d, J = 8.0 Hz, 1H), 7.33 (t, J = 7.5 Hz, 1H),
7.23 (d, J = 7.3 Hz, 1H), 7.17 (t, J = 8.5 Hz, 2H), 7.11 (d, J = 8.5 Hz,
J = 7.8 Hz, 1H), 7.87 (s, 1H), 7.81 (d, J = 7.6 Hz, 2H), 7.60 (d,
J = 7.8 Hz, 2H), 7.48 (t, J = 7.8 Hz, 2H), 7.44 (d, J = 8.0 Hz, 1H),
1
3
7
1
1
1
4
4
.41 (d, J = 7.5 Hz, 3H), 7.32 (t, J = 7.6 Hz, 1H), 7.22 (t, J = 7.6 Hz,
2H), 3.89 (s, 3H). C NMR (150 MHz, CDCl ) δ 161.3, 161.3, 161.0,
3
1
3
H), 2.46 (s, 3H). C NMR (150 MHz, CDCl
3
) δ 161.1, 155.9, 152.1,
155.0, 148.8, 142.3, 136.1, 130.7, 126.3, 126.2, 126.2, 124.4, 122.9,
42.3, 140.5, 139.1, 138.6, 135.7, 131.7, 130.2, 129.2, 128.6, 127.8,
122.7, 122.0, 115.6, 115.5, 115.1, 111.6, 111.1, 80.1, 55.5. MS (ESI):
+
26.3, 126.2, 124.4, 124.4, 123.0, 122.9, 111.0, 87.6, 18.4. MS (ESI):
436.15(C26
H18FN
5
O, [M + H] ). Anal. Calcd for C26
H
18FN O: C,
5
+
02.16(C26
H
19
N
5
, [M + H] ). Anal. Calcd for C26
H
19
5
N : C, 77.79; H,
71.71; H, 4.17; F, 4.36; N, 16.08; O, 3.67; Found: C, 71.70; H, 4.16; F,
4.35; N, 16.09; O, 3.65.
.77; N, 17.44; Found: C, 77.77; H, 4.76; N, 17.42.
7