G. Biagi et al. / Il Farmaco 56 (2001) 929–931
931
Table 2
Spectroscopic data of compounds 3–11
Comp. 1H NMR
Aromatic H
MS
Benzylic H
5.82 (s, 2H)
Aliphatic H
Exchang. H m/z (%)
3
4
5
6
7
8.50 (m, 2H); 7.53–7.48 (m,
5H), 7.36–7.32 (m, 3H)
8.50 (s, 2H); 7.49 (m, 2H); 7.31 5.80 (s, 2H)
(m, 2H)
8.49 (m, 2H); 7.49 (m, 5H);
7.39–7.22 (m, 8H)
8.50–8.45 (m, 3H); 7.61–7.27
(m, 12H)
5.18–5.05 (m, 1H, CH); 3.80 (s, 6.65 (1H)
3H, OCH3); 1.69 (d, 3H, CH3)
4.10 (t, 2H, CH2); 3.73 (s, 3H
OCH3); 2.83 (t, 2H, CH2)
5.40 (m, 1H, CH); 3.75 (s, 3H, 6.62 (1H)
CH3)
388 (M+, 2); 329 (8); 287 (1);
91 (100)
6.64 (1H)
388 (M+, 4); 329 (2); 91
(100)
5.80 (s, 2H);
3.37 (m, 2H)
6.05 (d, 1H);
5.81 (s, 2H)
5.83 (s, 2H)
464 (M+,0.5); 373 (13); 273
(18); 91 (100)
3.80 (s, 3H, OCH3)
7.11 (1H)
450 (M+, 2); 391 (7); 91
(100)
8.49 (m, 2H); 7.49 (m, 5H);
7.35 (m, 3H);
5.27 (m, 1H, CHN); 3.82 (s,
3H, OCH3); 3.65 (s, 3H,
OCH3); (t, 2H, CH2ꢀCO); 2.30
(m, 2H, CH2)
6.91 (1H)
460 (M+, 12); 387 (22); 287
(10); 91 (100)
8
8.52 (m, 2H); 7.52 (m, 5H);
7.35 (m, 3H)
5.83 (s, 2H)
5.82 (s, 2H)
5.82 (s, 2H)
5.83 (s, 2H)
5.33 (m, 1H, CH); 3.81 (s, 3H, 6.92 (1H)
OCH3); 2.68 (t, 2H, CH2ꢀS);
2.38 (m, 2H, CHꢀCH2); 2.12 (s,
3H, SꢀCH3)
5.15 (m, 1H, CH); 3.79 (s, 3H, 6.64 (1H)
OCH3); 1.98 (m, 2H, CH2);
1.50 (m, 2H, CH2); 0.99 (t, 3H,
CH3)
5.12 (m, 1H, CH); 3.79 (s, 3H, 6.66 (1H)
OCH3); 2.00 (m, 2H, CH2);
1.42 (m, 4H, CH2ꢀCH2); 0.91
(t, 3H)
374 (4); 287 (6); 91 (100); 61
(54)
9
8.51 (m, 2H); 7.50 (m, 5H);
7.35 (m, 3H)
357 (5); 302 (1); 91 (100)
371 (6); 302 (2); 91 (100)
357 (3); 302 (3.5); 91 (100)
10
11
8.51 (m, 2H); 7.51 (m, 5H);
7.35 (m, 3H)
8.51 (m, 2H); 7.50 (m, 5H);
7.35 (m, 3H)
5.14 (m, 1H, CHꢀN); 3.80 (s,
3H, OCH3); 2.42 (m, 1H, CH);
1.14 (d, 3H, CH3); 1.11 (d, 3H,
CH3)
6.66 (1H)
group on the carbon bound to N6 cannot give positive
interactions with the receptors.
azaadenines. Their affinity for A1 and A2 receptors. A compari-
son with the corresponding 2-phenyl-9-benzyl-8-azaadenosines,
Farmaco 50 (1995) 13–19.
[3] G. Biagi, I. Giorgi, O. Livi, V. Scartoni, A. Lucacchini, C.
Martini, P. Tacchi, N6-substituted 2-n-butil-9-benzyl-8-azaadeni-
nes. Affinity for A1 and A2 receptors. IV, Farmaco 49 (1994)
183–186.
Acknowledgements
[4] G. Biagi, I. Giorgi, O. Livi, V. Scartoni, A. Lucacchini, C.
Martini, P. Tacchi, N6-substituted 2-phenyl-9-benzyl-8-azaadeni-
nes. Affinity for A1 and A2 receptors. A comparison with 2-n-bu-
til analogous derivatives. V, Farmaco 49 (1994) 187–191.
[5] G. Biagi, I. Giorgi, O. Livi, V. Scartoni, C. Breschi, C. Martini,
R. Scatizzi, N6- or N(9)-substituted 2-phenyl-8-azaadenines:
affinity for A1 receptors, Farmaco 50 (1995) 659–667.
[6] G. Biagi, I. Giorgi, O. Livi, V. Scartoni, A. Lucacchini, N(9)-sub-
stituted 2-phenyl-N6-benzyl-8-azaadenines: A1 adenosine receptor
affinity. A comparison with the corresponding N6-substituted
2-phenyl-N(9)-benzyl-8-azaadenines, Farmaco 51 (1996) 395–399.
[7] P.L. Barili, G. Biagi, O. Livi, V. Scartoni, A facile ‘‘one pot’’
synthesis of 2,9-disubstituted 8-azapurin-6-ones (3,5-disubstituted
7-hydroxy-3-H-1,2,3-triazolo[4,5-d]pyrimidines), J. Heterocyclic
Chem. 22 (1985) 1607–1609.
This research was supported by the Ministero della
Ricerca Scientifica e Tecnologica (MURST).
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