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. 2022 Dec 14;66(1):890–912. doi: 10.1021/acs.jmedchem.2c01768

Table 6. Structure and Adenosine Receptor Affinities of Racemic and Enantiomers of Selected Ligands.

graphic file with name jm2c01768_0018.jpg

 
 Ki (nM) or % at 1 μM
compound R4 R3 R8 hA1a hA2Ab hA2Bc hA3d
(±)-ISAM-140 2-furyl i-Pr H 20% 28% 3.49 ± 0.2 2%
ISAM-140 2-furyl i-Pr H 14% 7% 17% 3%
(S)-ISAM-140 2-furyl i-Pr H 2% 12% 0.89 ± 0.2 4%
(±)-16b [(±)-ISAM-163] 2-furyl i-Pr F 21% 2% 3.05 ± 0.7 3%
(R)-16b(R)-ISAM-163] 2-furyl i-Pr F 15% 5% 41% 19%
(S)-16b [(S)-ISAM-163] 2-furyl i-Pr F 26% 11% 0.94 ± 0.1 12%
(±)-16j [(±)-ISAM-161] 2-furyl i-Pr Cl 35% 24% 5.03 ± 0.3 2%
(R)-16j [(R)-ISAM-161] 2-furyl i-Pr Cl 7% 37% 51% 5%
(S)-16j [(S)-ISAM-161] 2-furyl i-Pr Cl 48% 19% 2.04 ± 0.2 6%
(±)-16l [(±)-ISAM-M89A] 3-furyl i-Pr Cl 27% 176 ± 4 6.10 ± 0.7 1%
(S)-16l [(S)-ISAM-M89A] 3-furyl i-Pr Cl 24% 25% 53% 19%
(R)-16l [(R)-ISAM-M89A] 3-furyl i-Pr Cl 37% 96.3 ± 6 2.6 ± 0.3 24%
(±)-16r [(±)-ISAM-157] 2-furyl i-Pr Br 25% 2% 5.23 ± 0.4 10%
(R)-16r [(R)-ISAM-157] 2-furyl i-Pr Br 12% 7% 35% 2%
(S)-16r [(S)-ISAM-157] 2-furyl i-Pr Br 32% 14% 2.97 ± 0.4 6%
(±)-16s [(±)-ISAM-M114A] 3-furyl Et Br 1% 37% 3.32 ± 0.4 25%
(R)-16s [(R)-ISAM-M114A] 3-furyl Et Br 10% 12% 1.17 ± 0.1 14%
(S)-16s [(S)-ISAM-M114A] 3-furyl Et Br 11% 16% 34% 10%
(±)-18c [(±)-ISAM-R316A] 4-oxazolyl Et Cl 30% 13% 8.60 ± 0.4 15%
(R)-18c [(R)-ISAM-R316A] 4-oxazolyl Et Cl 9% 32% 26% 15%
(S)-18c [(S)-ISAM-R316A] 4-oxazolyl Et Cl 22% 17% 3.39 ± 0.2 6%
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 ± 9
a

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).

b

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).

c

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).

d

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).