1H NMR assignments for delavirdine and its metabolites3-a
| Proton | MET-4b | MET-4c | MET-16 | MET-5 | Delavirdine |
|---|---|---|---|---|---|
| Indole ring | |||||
| H-3 | 6.83 (s, 1H) | 6.85 (s, 1H) | 7.35 (d, 1H, J3-7 = 0.8 Hz) | 6.84 (s, 1H) | 6.88 (d, 1H, J3-7 = 0.8 Hz) |
| H-4 | 7.55 (s, 1H) | 7.56 (d, 1H, J4-6 = 1.9 Hz) | 7.56 (d, 1H, J4-6 = 1.9 Hz) | 7.58 (d, 1H, J4-6 = 2.1 Hz) | |
| H-6 | 7.17 (dd, 1H, J6-4 = <2 Hz, J6-7 = 8.5 Hz) | 7.17 (m, 1H) | 7.32 (d, 1H, J6-7 = 8.8 Hz) | 7.17 (m, 1H) | 7.17 (dd, 1H, J6-4 = 2.1 Hz, J6-7 = 8.8 Hz) |
| H-7 | 7.42 (d, 1H, J7-6 = 8.4 Hz) | 7.43 (d, 1H, J7-6 = 8.7 Hz) | 7.25 (dd, 1H, J7-6 = 8.7 Hz, J7-3 = 0.8 Hz) | 7.43 (d, 1H, J7-6 = 8.7 Hz) | 7.44 (d, 1H, J7-6 ± 8.8 Hz) |
| Pyridine ring | |||||
| H-4′ | 7.13 (d, 1H, J4′-5′ = 8.3 Hz) | 7.17 (m, 1H) | 6.98 (m, 1H) | 7.09 (dd, 1H, J4′-5′ = 7.8 Hz, J4′-6′ = 1.6 Hz) | 7.50 (dd, 1H, J4′-5′ = 8.3 Hz, J4′-6′ = 1.4 Hz) |
| H-5′ | 6.91 (d, 1H, J5′-4′ = 8.3 Hz | 7.01 (dd, 1H, J5′-4′ = 8.0 Hz, J5′-6′ = 4.9 Hz | 6.98 (m, 1H) | 6.90 (dd, 1H, J5′-4′ = 7.8 Hz, J5′-6′ = 4.9 Hz) | 7.37 (dd, 1H, J5′-4′ = 8.3 Hz, J5′-6′ = 5.7 Hz) |
| H-6′ | 7.68 (dd, 1H, J6′-4′ = 1.4 Hz, J6′-5′ = 4.9 Hz) | 7.55 (dd, 1H, J6′-4′ = 2.4 Hz, J6′-5′ = 4.0 Hz) | 7.62 (dd, 1H, J6′-4′ = 1.6 Hz, J6′-5′ = 4.8 Hz) | 7.60 (dd, 1H, J6′-4′ = 1.4 Hz, J6′-5′ = 5.7 Hz) | |
| Piperazine Ring | |||||
| CH2N | 3.99 (br s, 4H) | 4.07 (br s, 4H) | 4.08 (br s, 4H) | 4.13 (br s, 4H) | |
| CH2N | 3.19 (br s, 4H) | 3.03 (br d, 4H, J = 5.4 Hz) | 3.09 (m, 4H) | 3.15 (t, 4H, J = 5.0 Hz) | 3.39 (t, 4H, J = 5.1 Hz) |
| Isopropyl Chain | |||||
| CH | 3.65 (m, 1H) | 3.77 (m, 1H) | |||
| CH3 | 1.26 (d, 6H, J = 6.3 Hz) | 1.31 (d, 6H, J = 6.4 Hz) | |||
| Methylsulfonate | |||||
| CH2SO2NH | 2.88 (s, 3H) | 2.89 (s, 3H) | 2.93 (s, 3H) | 2.89 (s, 3H) | 2.89 (s, 3H) |
| Sugar | |||||
| H-1" | 5.91 (d, 1H, J1"-2" = 7.3 Hz) | 4.86 (d, 1H, J1"-2" = 7.9 Hz) | |||
| H-2" | 4.55 (dd, 1H, J2"-1" = 7.3 Hz, J2"-3" = 9.3 Hz) | 3.62 (dd, 1H, J2"-1" = 7.9 Hz, J2"-3" = 8.8 Hz) | |||
| H-3" | 4.01 (dd, 1H, J3"-2" = 9.3 Hz, J3"-4" = 10 Hz) | 3.47 (t, 1H, J3"-2" = 8.8 Hz J3"-4" = 8.8 Hz) | |||
| H-4" | 3.55 (dd, 1H, J4"-3" = 10 Hz, J4"-5" = 8.5 Hz) | 3.54 (t, 1H, J4"-3" = 8.8 Hz, J4"-5" = 9.5 Hz) | |||
| H-5" | 3.44 (m, 1H, J5"-4" = 8.5 Hz) | 3.59 (d, 1H, J5"-4" = 9.5 Hz) | |||
| H-6a" | 3.87 (dd, 1H, J6a"-6b" = 3.4 Hz, J6a"-6b" = 12 Hz) | ||||
| H-6b" | 3.67 (m, 1H, J6a"-6b" = 12 Hz) | ||||
| NHCOCH3 | 2.01 (s, 3H) | ||||
↵3-a Abbreviations: br s, broad singlet; d, doublet, dd, doublet of doublets, J, coupling constant in Hz; m, multiplet, s, singlet, t, triplet. In methanol-d4, chemical shift δ in ppm relative to methanol.