Med Chem Res
5
-{{1-[2-(4-Fluorophenyl)-2-oxo-ethyl]triazol-4-yl}methyl}-
CH Ph), 40.6 (CH , CH N\), 10.9 (CH ); Anal. calculated
for C H F N O ; C, 55.94; H, 3.41; N, 17.79. Found: C,
22 16 4 6 2
2
2
2
3
1
-methyl-3H-pyridazino[4,5-b]indol-4-one (7n) H NMR
1
(
400 MHz, CDCl ) d 7.19–7.87 (10H, m, Ar–H), 6.25 (2H,
55.82; H, 3.49; N, 17.83.
3
s, NCH -Ar), 5.79 (2H, s, NCH COPh), 2.63 (3H, s, Ar–
2
2
4
5
-{{4-[(8-Fluoro-1-methyl-4-oxo-3,4-dihydropyridazino[4,
1
3
CH3); C NMR (100 MHz, CDCl ) d 184.9 (C, COPh),
3
-b]indol-5-yl)methyl]-1H-1,2,3-triazol-1-yl}methyl}ben-
1
1
1
1
61.0 (C, C=O), 160.5, 159.7, 158.6, 148.7, 141.5, 139.3,
35.6, 128.5, 124.1, 123.0, 122.7, 122.0, 121.1, 120.3,
19.3, 116.7, 114.3 (Ar–C), 50.6 (CH , CH COPh), 40.9
zonitrile (7s) H NMR (300 MHz, CDCl ) d 7.13–7.87
3
(
8H, m, Ar–H), 5.99 (2H, s, NCH -Ar), 5.51 (2H, s, NCH -
2 2
2
2
13
Ph), 2.66 (3H, s, Ar–CH3); C NMR (100 MHz, CDCl ) d
3
(
CH , CH N\), 10.4 (CH ); Anal. calculated for C H
2
2
3
22 17
1
1
1
63.2 (C, C=O), 159.8, 157.4, 144.9, 139.6, 135.7, 132.8,
28.4, 127.1, 127.0, 123.4, 123.3 (Ar–C), 118.1 (C, CN),
14.2, 113.9, 112.7, 112.5, 106.7, 106.1 (Ar–C), 53.4 (CH2,
FN O ; C, 63.46; H, 4.11; N, 20.18. Found: C, 63.65; H,
6
2
4
.02; N, 20.24.
5
-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-8-fluoro-1-methyl-
1
H-pyridazino[4,5-b]indol-4(5H)-one (7o) H NMR
CH Ph), 40.5 (CH , CH N\), 11.0 (CH ); MS (m/z) 414.1
(M ? H) ; Anal. calculated for C H FN O; C, 63.92; H,
22 16 7
2
2
2
3
?
3
(
400 MHz, CDCl ) d 7.11–7.82 (10H, m, Ar–H), 6.11 (2H,
3.90; N, 23.72. Found: C, 64.04; H, 3.94; N, 23.63.
3
s, NCH -Ar), 5.44 (2H, s, NCH -Ph), 2.64 (3H, s, Ar–
2
2
5
-{[1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-8-fluoro-
1
1
3
CH3); C NMR (100 MHz, CDCl ) d 161.0 (C, C=O),
3
1
-methyl-3H-pyridazino[4,5-b] indol-4(5H)-one (7t)
H
1
1
1
1
4
60.8, 157.3, 145.9, 140.4, 136.1, 130.8, 129.2, 128.9,
27.5, 127.0, 126.6, 124.9, 122.8, 122.3, 121.6, 110.9,
08.3 (Ar–C), 54.8 (CH , CH Ph), 40.7 (CH , CH N\),
NMR (300 MHz, CDCl ) d 7.13–8.21 (9H, m, Ar–H), 5.99
3
(
2H, s, NCH -Ar), 5.55 (2H, s, NCH -Ph), 2.66 (3H, s, Ar–
2 2
2
2
2
2
13
CH3); C NMR (100 MHz, CDCl ) d 162.0 (C, C=O),
3
0.0 (CH ); Anal. calculated for C H FN O; C, 64.94; H,
3
21 17
6
1
60.7, 159.6, 157.1, 145.1, 141.9, 138.1, 132.2, 131.6,
.41; N, 21.64. Found: C, 65.10; H, 4.32; N, 21.60.
1
31.1, 130.9, 130.1, 127.6, 127.1, 125.6, 123.6, 120.6,
5
-{[1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl]methyl}-8-
119.6 (Ar–C), 54.5 (CH , CH Ph), 40.1 (CH , CH N\),
2
2
2
2
fluoro-1-methyl-3H-pyridazino
1
[4,5-b]indol-4(5H)-one
10.6 (CH ); Anal. calculated for C H FN O ; C, 58.20;
3 21 16 7 3
(
7p) H NMR (400 MHz, CDCl ) d 7.08–7.92 (9H, m,
H, 3.72; N, 22.62. Found: C, 58.28; H, 3.69; N, 22.58.
-{[1-(4-Fluorobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-8-flu-
3
Ar–H), 5.95 (2H, s, NCH -Ar), 5.34 (2H, s, NCH -Ph),
2
2
5
1
3
3
.77 (3H, s, OCH ), 2.64 (3H, s, Ar–CH ); C NMR
3 3
oro-1-methyl-3H-pyridazino[4,5-b] indol-4(5H)-one (7u)
1
(
100 MHz, CDCl ) d 163.0 (C, C=O), 159.8, 159.6, 157.4,
3
H NMR (400 MHz, CDCl ) d 7.11–7.94 (9H, m, Ar–H),
3
1
44.3, 135.7, 129.5, 127.1, 127.0, 126.5, 123.4, 122.6,
6
.01 (2H, s, NCH -Ar), 5.50 (2H, s, NCH -Ph), 2.63 (3H, s,
2 2
1
14.4, 114.0, 113.7, 112.7, 106.6, 106.2 (Ar–C), 58.3 (CH3,
13
Ar–CH3); C NMR (100 MHz, CDCl ) d 165.6 (C, C-F),
3
OMe), 53.7 (CH , CH Ph), 40.6 (CH , CH N\), 11.0
2
2
2
2
1
1
1
63.0 (C, C=O), 162.8, 160.6, 159.1, 146.6, 142.3, 132.8,
30.9, 130.1, 128.5, 126.6, 124.1, 123.2, 122.4, 122.0,
16.0, 112.6 (Ar–C), 52.5 (CH , CH Ph), 40.9 (CH ,
(
CH ). Anal. calculated for C H FN O ; C, 63.15; H,
3 22 19 6 2
4
.58; N, 20.08. Found: C, 63.29; H, 4.49; N, 20.11.
2
2
2
5-{{1-[4-(Trifluoromethyl)benzyl]-1H-1,2,3-triazol-4-yl}me-
CH N\), 10.3 (CH ); Anal. calculated for C H F N O;
2
3
21 16 2 6
thyl}-8-fluoro-1-methyl-3H-pyridazino[4,5-b]indol-4(5H)-
1
C, 62.06; H, 3.97; N, 20.68. Found: C, 62.19; H, 3.90; N,
one (7q) H NMR (300 MHz, CDCl ) d 7.16–7.87 (8H,
20.62.
3
m, Ar–H), 5.99 (2H, s, NCH -Ar), 5.51 (2H, s, NCH -Ph),
2
2
1
.65 (3H, s, Ar–CH3); C NMR (100 MHz, CDCl3)
3
5-{[1-(2-Fluorobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-8-flu-
1
oro-1-methyl-3H-pyridazino[4,5-b]indol-4(5H)-one (7v) H
2
d 163.1 (C, C=O), 159.8, 159.6, 157.4, 144.8, 138.4, 135.7,
NMR (400 MHz, CDCl ) d 7.11–7.94 (9H, m, Ar–H), 6.08
3
1
28.1, 127.1, 127.0, 126.0 (Ar–C), 124.4 (C, CF ), 123.3,
3
(
2H, s, NCH -Ar), 5.56 (2H, s, NCH -Ph), 2.61 (3H, s, Ar–
2 2
1
23.2, 114.1, 113.9, 112.6, 106.7, 106.0 (Ar–C), 53.4 (CH2,
1
3
CH3); C NMR (100 MHz, CDCl ) d 165.0 (C, C-F),
163.6 (C, C=O), 161.6, 161.1, 159.0, 140.2, 133.1, 132.8,
3
CH Ph), 40.6 (CH , CH N\), 11.0 (CH ); MS (m/z) 457.1
2
2
2
3
?
M ? H) ; Anal. calculated for C H F N O; C, 57.90;
(
22 16 4 6
1
1
29.3, 128.4, 124.8, 124.0, 123.9, 122.7, 117.1, 116.3,
13.2, 109.8 (Ar–C), 47.7 (CH , CH Ph), 40.5 (CH ,
H, 3.53; N, 18.41. Found: C, 57.79; H, 3.58; N, 18.47.
-{{1-[4-(Trifluoromethoxy)benzyl]-1H-1,2,3-triazol-4-yl}
methyl}-8-fluoro-1-methyl-3H-pyridazino[4,5-b]indol-4(5H)-
2
2
2
5
CH N\), 10.8 (CH ); Anal. calculated for C H F N O;
C, 62.06; H, 3.97; N, 20.68. Found: C, 62.18; H, 4.00; N,
2
3
21 16 2 6
1
one (7r) H NMR (400 MHz, CDCl ) d 7.11–7.84 (8H,
3
20.60.
m, Ar–H), 5.97 (2H, s, NCH -Ar), 5.42 (2H, s, NCH -Ph),
2
2
1
.64 (3H, s, Ar–CH3); C NMR (100 MHz, CDCl3)
3
2
5-[(1-Cyclopentyl-1H-1,2,3-triazol-4-yl)methyl]-8-fluoro-
1
d 163.1 (C, C=O), 159.8, 157.4, 149.4, 144.6, 135.7, 134.3,
1-methyl-3H-pyridazino[4,5-b] indol-4(5H)-one (7w)
NMR (300 MHz, CDCl
(2H, s, NCH -Ar), 4.81–4.86 (1H, m, NCH\), 2.66 (3H, s,
H
1
1
33.2, 131.3, 130.9, 129.8, 128.8, 123.3, 125.6, 123.1,
21.6, 121.5 (Ar–C), 121.2 (C, OCF ), 119.1, 53.2 (CH ,
3
) d 7.08–7.79 (4H, m, Ar–H), 6.05
3
2
2
123