Phenylazoxanthines are less potent than corresponding styrylxanthine derivatives. In styrylxanthines, methylation in the N7 position increases A_2A-AR affinity, while decreasing A₁-affinity. In azo analogs, A_2A-affinity is also increased by 7-methylation of the xanthine structure (from 19 to 27-fold), but A₁-affinity is increased as well, although to smaller extent (about 3-fold). As observed for styrylcaffeines, a meta-chloro substituent on the phenyl ring increased A_2A-affinity about 2-fold, virtually without having any effect on A₁-affinity, thus increasing A_2A-selectivity. In azo analogs group the presence of chloro- or bromo-substituents makes no differneces in affinity.

With the aim to find the nature of those differnces we did an x-ray analysis of 8-fenylazo-7-methylxanthine. Than we made molecular modelling calculations of this derivative and other azo-anologs as well as corresponding styrylxanthines in 2 data bases.

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