Y. Kitade et al. / Tetrahedron Letters 42 (2001) 433–435
435
B
soft base
N3
soft base
N3
pathway a
pathway b
cis-elimination
trans-elimination
O
O
c
Hb
d
Hc
MsO
B
MsO
B
10
a
b
O
O
O
O
Ha
Ha
OBut
hard base
B
OBut
hard base
5
9
pathway c
pathway d
trans-elimination
trans-elimination
O
O
12
Scheme 3.
The structure of these compounds (2–13) was fully
supported by spectral data (1H NMR, 13C NMR, MS,
and HRMS).8 Compound 11 showed inhibitory effect
against human recombinant SAH hydrolase9 with IC50
value of 15 mM.10
1849–1851. (b) Obara, T.; Shuto, S.; Saito, Y.; Snoeck,
R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Matsuda, A.
J. Med. Chem. 1996, 39, 3847–3852.
8. Selected data for 10: 1H NMR (CDCl3, 400 MHz): l 1.41
(6H, s, isopropylidene), 2.79–2.93 (2H, m, H-5%), 4.90
(1H, t, J=5.6 Hz, H-1%), 5.47 (1H, d, J=6.0 Hz, H-2%),
6.33 (2H, brs, NH2), 6.68 (1H, m, H-4%), 8.28 and 8.39
(each 1H, each s, H-2 and H-8). MS m/z (%): 273 (M+,
28), 215 (100), 186 (63). HRMS m/z: 273.1219 (C1
3H15N5O2, requires 273.1226). Selected data for 11: 1H
NMR (D2O, 400 MHz): l 2.73 (1H, d, J=16.8 Hz,
H-5%), 2.73 (1H, d, J=16.8 Hz, H-5%), 4.37 (1H, m, H-1%),
4.94 (1H, d, J=5.2 Hz, H-2%), 6.37 (1H, s, H-4%), 8.27 and
8.32 (each 1H, each s, H-2 and H-8). MS m/z (%): 233
(M+, 36), 204 (100), 186 (21). HRMS m/z: 233.0919
(C10H11N5O2, requires 233.0913). Selected data for 12: 1H
NMR (CDCl3, 400 MHz): l 1.34 (3H, s, isop), 1.48 (3H,
s, isop), 4.68 (1H, d, J=5.2 Hz, H-2%), 5.47 (1H, d,
J=5.2 Hz, H-1%), 5.62 (1H, s, H-3%), 5.94 (1H, dd,
J=6.0, 1.0 Hz, H-5%), 6.05 (2H, brs, NH2), 6.31 (1H, dd,
J=6.0, 1.0 Hz, H-4%), 7.66 and 8.36 (each 1H, each s,
H-2 and H-8). 13C NMR (CDCl3, 100 MHz): l 25.73,
27.33, 65.65, 83.93, 84.67, 112.42, 119.89, 129.32, 138.41,
138.70, 149.96, 152.49, 155.10. MS m/z (%): 273 (M+, 12),
215 (100), 186 (86). HRMS m/z: 273.1220 (C13H15N5O2,
requires 273.1226). Selected data for 13 (DHCeA): 1H
NMR ((CD3)2SO, 400 MHz): l 4.30 (1H, m, H-2%), 4.54
(1H, d, J=3.2 Hz, H-3%), 5.38 (1H, d, J=5.8 Hz, H-1%),
5.98 (1H, m, H-5%), 6.13 (1H, m, H-4%), 7.42 (2H, brs,
NH2), 8.12 and 8.15 (each 1H, each s, H-2 and H-8). 13C
NMR ((CD3)2SO, 100 MHz): l 64.76, 72.49, 76.16,
119.75, 132.30, 136.02, 140.02, 151.36, 155.27. MS m/z
(%): 233 (M+, 8), 136 (100), 108 (13). HRMS m/z:
233.0913 (C10H11N5O2, requires 233.0913)
Acknowledgements
This research was in part supported by a Grant-in-Aid
for Scientific Research No. 10672086; Grants-in-Aid for
Scientific Research on Priority Area No. 10169222 and
11147211 from the Ministry of Education, Science,
Culture and Sports and a grant from the Gifu Life
Science Research Promotion Council.
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