9
-Sulfonyl-9(H)-purine Derivatives Inhibit HCV Replication
39
1
1
H), 5.37 (dd, J = 16.9, 1.1 Hz, 1H), 5.16 (d, J = 10.0 Hz,
165.51, 153.44, 148.95, 144.27, 142.37, 134.82, 131.39,
13
H), 4.03 (d, J = 6.8 Hz, 2H), 2.44 (s, 3H). C NMR
127.13, 114.99, 55.96. HRMS m/z calculated for
+
C H BrN NaO S [M+ Na] : 390.9471, found 390.9459.
(
100 MHz, CDCl ), d (ppm): 162.24, 153.37, 147.34,
3
12
9
4
3
1
47.08, 140.18, 133.68, 132.67, 131.55, 130.27, 128.62,
6-Iodo-9-((4-methoxyphenyl)sulfonyl)-9H-purine
1
(3n). H NMR (400 MHz, CDCl ), d (ppm): 8.72 (s, 1H),
118.65, 31.57, 21.83. HRMS m/z calculated for
3
+
C H N NaO S [M+Na] : 369.0450, found 369.0441.
8.59 (s, 1H), 8.22 (d, J = 8.5 Hz, 2H), 7.04 (d, J = 8.5 Hz,
13
2H), 3.88 (s, 3H). C NMR (100 MHz, CDCl ), d (ppm):
1
5
14
4
2 2
1
N,N-dimethyl-9-tosyl-9H-purin-6-amine (3g).
NMR (400 MHz, CDCl ), d (ppm): 8.41 (s, 1H), 8.19 (s,
H
3
165.46, 153.42, 146.48, 141.83, 139.05, 131.36, 127.15,
3
1
H), 8.12 (d, J = 7.9 Hz, 2H), 7.34 (d, J = 7.9 Hz, 2H), 3.48
123.04, 114.98, 55.97. HRMS m/z calculated for
+
C H IN NaO S [M+ Na] : 438.9332, found 438.9353.
13
(
s, 6H), 2.41 (s, 3H). C NMR (100 MHz, CDCl ), d (ppm):
3
12
9
4
3
1
54.45, 153.59, 149.62, 146.53, 135.66, 134.06, 130.03,
6-Chloro-9-((4-isopropoxyphenyl)sulfonyl)-9H-pu-
1
rine (3o). H NMR (400 MHz, CDCl ), d (ppm): 8.87 (s,
1
28.53, 120.19, 38.63, 21.77. HRMS m/z calculated for
3
+
C H N NaO S [M+ Na] : 340.0839, found 340.0822.
1H), 8.60 (s, 1H), 8.21 (d, J = 9.1 Hz, 2H), 7.00 (d,
J = 9.1 Hz, 2H), 4.67 (q, J = 6.0 Hz, 1H), 1.37 (d, J = 6.1 Hz,
1
4
15
5
2
1
N,N-diethyl-9-tosyl-9H-purin-6-amine (3h). H NMR
1
6H). C NMR (100 MHz, CDCl ), d (ppm): 164.14, 153.52,
3
(
400 MHz, CDCl ), d (ppm): 8.42 (s, 1H), 8.20 (s, 1H), 8.15
3
3
(
d, J = 8.4 Hz, 2H), 7.36 (d, J = 8.2 Hz, 2H), 3.93 (d,
152.17, 150.20, 142.58, 132.26, 129.60, 126.28, 116.04,
1
3
J = 8.4 Hz, 4H), 2.42 (s, 3H), 1.26 (s, 6H). C NMR
71.11, 21.71. HRMS m/z calculated for C H ClN NaO S
+
1
4
13
4
3
(
100 MHz, CDCl ), d (ppm): 154.52, 153.66, 149.63,
[M+Na] : 375.0289, found 375.0296.
9-((4-(Tert-butyl)phenyl)sulfonyl)-6-chloro-9H-pu-
3
1
1
3
46.50, 135.77, 134.11, 130.03, 128.59, 119.64, 21.78,
+
3.12. HRMS m/z calculated for C H N NaO S [M+Na] :
1
rine (3p). H NMR (400 MHz, CDCl ), d (ppm): 8.80 (s,
16
19
5
2
3
68.1152, found 368.1159.
-(9-Tosyl-9H-purin-6-yl)morpholine (3i). H NMR
1H), 8.51 (s, 1H), 8.14 (d, J = 8.7 Hz, 2H), 7.54 (d,
13
J = 8.7 Hz, 2H), 1.24 (s, 9H). C NMR (100 MHz, CDCl3),
1
4
(
400 MHz, CDCl ), d (ppm): 8.42 (s, 1H), 8.21 (s, 1H), 8.13
d (ppm): 160.40, 153.65, 152.27, 150.28, 142.55, 133.09,
132.29, 128.64, 126.89, 35.59, 30.88. HRMS m/z calculated
3
(
d, J = 8.3 Hz, 2H), 7.35 (d, J = 8.2 Hz, 2H), 4.25 (s, 4H),
1
3
+
for C H ClN O S [M+H] : 351.0677, found 351.0670.
3
.88 – 3.65 (m, 4H), 2.42 (s, 3H). C NMR (100 MHz,
1
5
16
4
2
CDCl ), d (ppm): 154.58, 153.65, 149.99, 146.66, 135.99,
6-Chloro-9-((3-(trifluoromethyl)phenyl)sulfonyl)-9H-
1
purine (3q). H NMR (400 MHz, CDCl ), d (ppm): 8.89 (s,
3
1
33.94, 130.07, 128.60, 120.02, 66.87, 45.75, 21.79. HRMS
3
+
m/z calculated for C H N NaO S [M+Na] : 382.0944,
1H), 8.63 (d, J = 5.5 Hz, 2H), 8.57 (d, J = 8.1 Hz, 1H), 8.02
16
17
5
3
1
(d, J = 7.9 Hz, 1H), 7.82 (t, J = 7.9 Hz, 1H). C NMR
3
found 382.0958.
-Chloro-9-((4-methoxyphenyl)sulfonyl)-9H-purine
6
(100 MHz, CDCl ), d (ppm): 153.80, 152.69, 150.13,
3
1
3j). H NMR (400 MHz, CDCl ), d (ppm): 8.86 (s, 1H),
(
142.05, 137.35, 132.52, 132.49, 132.35, 132.09, 130.70,
3
8
2
1
1
.60 (s, 1H), 8.24 (d, J = 8.7 Hz, 2H), 7.05 (d, J = 8.7 Hz,
126.13, 126.09. HRMS m/z calculated for C H ClF N O S
+
[M+H] : 362.9925, found 362.9946.
1
2
7
3
4
2
1
3
H), 3.90 (s, 3H). C NMR (100 MHz, CDCl ), d (ppm):
3
65.50, 153.55, 152.20, 150.16, 142.55, 132.24, 131.40,
6-Chloro-9-((4-nitrophenyl)sulfonyl)-9H-purine (3r).
1
27.04, 115.00, 55.99. HRMS m/z calculated for
H NMR (400 MHz, DMSO-d ), d (ppm): 8.76 (s, 1H), 8.72
6
+
C H ClN O S [M+H] : 325.0157, found 325.0160.
(s, 1H), 8.21 (d, J = 8.8 Hz, 2H), 7.86 (d, J = 8.8 Hz, 2H).
13
C NMR (100 MHz, DMSO-d ), d (ppm): 154.20, 151.54,
1
2
10
4
3
1
H
9
-((4-Methoxyphenyl)sulfonyl)-9H-purine (3k).
6
NMR (400 MHz, CDCl ), d (ppm): 9.08 (s, 1H), 9.02 (s,
147.24, 146.09, 126.88, 123.30. HRMS m/z calculated for
+
C H ClN O S [M+H] : 339.9902, found 339.9900.
3
1
H), 8.49 (s, 1H), 8.17 (d, J = 9.0 Hz, 2H), 6.96 (d,
11
7
5
4
13
J = 9.0 Hz, 2H), 3.81 (s, 3H). C NMR (100 MHz, CDCl3),
d (ppm): 165.31, 153.97, 150.03, 149.46, 142.68, 134.47,
31.25, 127.51, 114.90, 55.92. HRMS m/z calculated for
6-Chloro-9-((3-nitrophenyl)sulfonyl)-9H-purine (3s).
H NMR (400 MHz, DMSO-d ), d (ppm): 8.76 (s, 1H), 8.72
1
6
1
(s, 1H), 8.36 (s, 1H), 8.20 (dd, J = 8.1, 1.6 Hz, 1H), 8.04 (d,
13
+
C H N O S [M+H] : 291.0546, found 291.0548.
J = 7.6 Hz, 1H), 7.67 (t, J = 7.9 Hz, 1H).
C NMR
1
2
11
4
3
9
-((4-Methoxyphenyl)sulfonyl)-9H-purin-6-amine
(100 MHz, DMSO-d ), d (ppm): 153.97, 151.53, 149.94,
6
1
3l). H NMR (400 MHz, CDCl ), d (ppm): 8.35 (s, 1H),
(
147.72, 147.19, 146.10, 131.93, 129.74, 129.12, 123.34,
+
120.03. HRMS m/z calculated for C H ClN O S [M+H] :
3
8
.23 (s, 1H), 8.14 (d, J = 9.0 Hz, 2H), 6.95 (d, J = 8.8 Hz,
11
7
5
4
1
3
2
H), 6.13 (s, 2H), 3.80 (s, 3H). C NMR (100 MHz,
339.9902, found 339.9903.
CDCl ), d (ppm): 165.13, 138.59, 131.15, 127.55, 119.89,
6-Chloro-9-((2-nitrophenyl)sulfonyl)-9H-purine (3t).
3
1
1
14.79, 55.89. HRMS m/z calculated for C H N NaO S
+
H NMR (400 MHz, CDCl ), d (ppm): 8.89 – 8.83 (m, 1H),
12
11
5
3
3
[
M+ Na] : 328.0475, found 328.0472.
-Bromo-9-((4-methoxyphenyl)sulfonyl)-9H-purine
8.82 (s, 1H), 8.65 (s, 1H), 8.01 – 7.92 (m, 2H), 7.91 – 7.84
1
(m, 1H). C NMR (100 MHz, CDCl ), d (ppm): 153.62,
3
6
3
1
3m). H NMR (400 MHz, CDCl ), d (ppm): 8.80 (s, 1H),
(
152.43, 150.21, 148.29, 143.39, 137.03, 134.64, 132.98,
3
8
.59 (s, 1H), 8.22 (d, J = 9.0 Hz, 2H), 7.04 (d, J = 9.0 Hz,
132.09, 128.99, 125.40. HRMS m/z calculated for
+
C H ClN O S [M+H] : 339.9902, found 339.9903.
1
H), 3.88 (s, 4H). C NMR (100 MHz, CDCl ), d (ppm):
3
2
3
11
7
5
4