Table 2.
1H-NMR (DMSO-d6) chemical shifts (δ/ppm) and H-H coupling constants (J/Hz) in 1H-NMR spectra for compounds 14–18 (for enumeration of atoms c.f. Figure 1).
| OH-2" | H-8 | H-5 | H-6" | H-5" | H-3" | OH-4' | OMe-4" | H-1' | H-2' | H-3' | H-4' | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 14 a | 9.64 (s, 1H) | / | 8.11 (s, 1H) | 6.88 (AB, dd, 1H, J= 3.27, 8.43) | 6.36 (AB, dd, 1H, J = 2.34, 8.36) | 6.36 (d, 1H, J = 8.30) | 5.19 (t, 1H, J = 6.03) | 3.65 (s, 3H) | 3.17–3.24 (m, 2H) | 2.52–2.56 (m, 1H) | 1.80–1.61 (m, 2H) | 4.15–4.18 (m, 2H) |
| 15 b | 9.49 (s, 1H) | / | 8.25 (s, 1H) | 6.91 (d, 1H, J = 8.37) | 6.35 (d, 1H, J = 2.31) | 6.30 (AB, dd, 1H, J= 2.28, 8.34) | 5.11 (t, 1H, J = 6.01) | 3.65 (s, 3H) | 3.16–3.18 (m, 2H) | 2.32–2.35 (m, 1H) | 1.79–1.61 (m, 2H) | 4.37–4.40 (m, 2H) |
| 16 c | 9.47 (s, 1H) | / | 8.17 (s, 1H) | 6.87 (d, 1H, J = 8.40) | 6.34 (d, 1H, J = 2.28) | 6.28 (AB, dd, 1H, J = 2.28, 8.40) | 5.14 (t, 1H, J = 5.96) | 3.65 (s, 3H) | 3.25–3.17 (m, 2H) | 2.84–2.87 (m, 1H) | 1.79–1.61 (m, 2H) | 4.27–4.29 (m, 2H) |
| 17 d | 9.42 (s, 1H) | / | 8.07 (s, 1H) | 6.91 (d, 1H, J = 8.40) | 6.36 (d, 1H, J = 2.46) | 6.31 (AB, dd, 1H, J = 2.40, 8.34) | 5.11 (t, 1H, J = 6.06) | 3.66 (s, 3H) | 3.21–3.13 (m, 2H) | 2.33–2.37 (m, 1H) | 1.79–1.61 (m, 2H) | 4.34–4.37 (m, 2H) |
| 18 e | 9.46 (s, 1H) | 7.2 (s, 1H) | / | 6.92 (d, 1H, J = 8.34) | 6.32 (d, 1H, J = 1.95) | 6.29 (AB, dd, 1H, J = 2.35, 8.19) | 4.97 (t, 1H, J = 6.04) | 3.66 (s, 3H) | 3.26–3.17 (m, 2H) | 3.04–3.07 (m, 1H) | 1.82–1.62 (m, 2H) | 4.13– 4.16 (m, 2H) |
a Compound 14: signal for COOCH2CH3-triazole: 2.70 ppm (m, 2H); COOCH2CH3-triazole: 1.05 ppm (t, 3H,J = 7.1 Hz); b Compound 15: signal for CONH2-triazole: 7.69 and 7.50 ppm (2 × s, 2 × 1H); c Compound 16: signal for H-3: 7.88 ppm (s, 1H); d Compound 17: signal for OH-3-triazole: 4.37 ppm (d, 1H,J = 6.0 Hz); CH2-3-triazole: 4.30 (d, 2H, J = 7.4 Hz); e Compound 18: signal for NH-purine: 10.70 ppm (s, 1H); NH2-purine: 6.56 ppm (s, 2H).