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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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8-Substituted xanthines as antagonists at A1- and A2-adenosine receptors.

Two classes of 8-substituted analogs of theophylline (1,3-dialkylxanthines), having 8-cycloalkyl, 8-cycloalkenyl or 8-(para-substituted aryl) groups, were shown to be potent and, in some cases, receptor subtype selective antagonists at A1- and A2-adenosine receptors. New analogs based on a functionalized cogener approach and on classical medicinal chemical approaches were prepared. Affinity at A1-adenosine receptors was evaluated by inhibition of binding of [3H]N6-phenylisopropyladenosine to rat brain membranes. Activity at A2-adenosine receptors was measured by the reversal of 5'-N-ethylcarboxamidoadenosine (NECA)-stimulated production of cyclic AMP in membranes from rat pheochromocytoma PC12 cells. Cycloalkenyl analogs containing rigid olefinic bonds differed greatly in potency from the saturated analogs. The selectivity of phenylsulfonamide analogs depended on distal structural features. Novel xanthine analogs include diamino-, thiol-, aldehyde, and halogen-substituted derivatives, peptide conjugates of 8-[4-[2-aminoethylaminocarbonylmethyloxy]phenyl]1,3-dipropylxan thi ne (XAC), and a hydroxyethylamide analog of XAC.[1]

References

  1. 8-Substituted xanthines as antagonists at A1- and A2-adenosine receptors. Jacobson, K.A., de la Cruz, R., Schulick, R., Kiriasis, L., Padgett, W., Pfleiderer, W., Kirk, K.L., Neumeyer, J.L., Daly, J.W. Biochem. Pharmacol. (1988) [Pubmed]
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