Journal of Medicinal Chemistry p. 924 - 930 (1992)
Update date:2022-08-04
Topics:
Shimada
Suzuki
Nonaka
Ishii
With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3- noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6- substituent of adenosine agonists appears to bind to the same region of the A1 receptor.
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