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. Author manuscript; available in PMC: 2024 Jan 17.
Published in final edited form as: J Med Chem. 2002 Aug 1;45(16):3440–3450. doi: 10.1021/jm011093d

Table 6.

Functional Antagonist Activity of Selected Imidazopurinones at A1, A2A, and A2B ARs in Comparison with Standard Xanthine Derivatives

graphic file with name nihms-1958395-t0008.jpg
compd R1 R2 R4 R8 KB ± SEM (μM)
A1 A2A A2B
Imidazopurinones
21 methyl phenyl H H 0.50 ± 0.11 17 ± 2 7.0 ± 0.3
R-24 H phenyl methyl (R)-ethyl 0.43 ± 0.10 2.5 ± 0.2 2.1 ± 0.3
S-24 H phenyl methyl (S)-ethyl 0.063 ± 0.021 4.3 ± 0.1 7.6 ± 7.3
S-25 methyl styryl methyl (S)-ethyl 33 ± 10 1.0 ± 0.1 3.7 ± 0.3
Xanthines
R7 R8 R3 R1
11f methyl phenyl H methyl 0.32 ± 0.03 5.7 ± 0.7 5.2 ± 0.9
caffeine methyl H methyl methyl 60a 36 ± 4a 25 ± 2
theophylline H H methyl methyl 8.7a 13.7 ± 0.4a 16 ± 8
enprofylline H H propyl H 32 ± 2b 120 ± 17a 18 ± 4
a

Data from Choi; et al. Life Sci. 1988, 43, 387–398; Hide; et al. Mol. Pharmacol. 1992, 41, 352–359; Ukena; et al. Life Sci. 1986, 39, 743–750; and Brackett; Daly. Biochem. Pharmacol. 1994, 47, 801–804.

b

Binding data: Rat cerebral cortical membranes, [3H]R-PIA. Müller; et al. J. Med. Chem. 1993, 36, 3341–3349; also, 81 μM. Shamim; et al. J. Med. Chem. 1989, 32, 1231.