Table 5. Structure and Adenosine Receptor Affinities of Series IV: Alkyl 7/8-Halo 4-(oxazol-4-yl)-1,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates (Cmpds 17a–d and 18a–d).
| |
Ki (nM) or % at 1 μM |
||||||
|---|---|---|---|---|---|---|---|
| compound | R3 | X | hA1a | hA2Ab | hA2Bc | hA3d | |
| 17a | Et | 7-F | 43% | 4% | 44.7 ± 1.4 | 26% | |
| 17b (ISAM-R324B) | i-Pr | 7-F | 34% | 19% | 7.60 ± 0.6 | 22% | |
| 17c | Et | 7-Cl | 227 nM | 14% | 25.6 ± 1.2 | 11% | |
| 17d | i-Pr | 7-Cl | 27% | 1% | 102 ± 7 | 20% | |
| 18a | Et | 8-F | 25% | 16% | 14.7 ± 1.1 | 16% | |
| 18b (ISAM-R324A) | i-Pr | 8-F | 29% | 20% | 6.10 ± 0.3 | 20% | |
| 18c (ISAM-R316A) | Et | 8-Cl | 30% | 13% | 8.60 ± 0.4 | 15% | |
| 18d (ISAM-R319A) | i-Pr | 8-Cl | 23% | 35% | 6.40 ± 0.7 | 23% | |
| DPCPX | 2.20 ± 0.2 | 157 ± 3 | 73.2 ± 1.4 | 1722 ± 11 | |||
| ZM241385 | 683 ± 4 | 1.9 ± 0.1 | 65.7 ± 1.1 | 863 ± 4 | |||
| NECA | 14.0 ± 1 | 20.0 ± 3 | 2400 ± 35 | 6.20 ± 0.9 | |||
Displacement of specific [3H]DPCPX binding in human CHO cells expressed as Ki in nanomolars (n = 3) or percentage displacement of specific binding at a concentration of 1 μM (n = 2).
Displacement of specific [3H]4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-a][1,3,5]triazin-5-ylamino]ethyl)phenol binding in human HeLa cells expressed as Ki in nanomolars (n = 3) or percentage displacement of specific binding at a concentration of 1 μM (n = 2).
Displacement of specific [3H]DPCPX binding in human HEK-293 cells expressed as Ki in nanomolars (n = 3) or percentage displacement of specific binding at a concentration of 1 μM (n = 2).
Displacement of specific [3H]NECA binding in human HeLa cells expressed as Ki in nanomolars (n = 3) or percentage displacement of specific binding at a concentration of 1 μM (n = 2).