191349-79-8Relevant academic research and scientific papers
Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1- adenosine receptor antagonists
Ceccarelli, Stefano,D'Alessandro, Alessandra,Prinzivalli, Michela,Zanarella, Sergio
, p. 943 - 955 (1998)
The syntheses and A1 adenosine receptor affinities of a number of imidazo[1,2-a]quinoxalin-4-amines are reported. Structure-activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A1 adenosine receptors. Secondary amino compounds displayed the best affinities toward A1 receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for 1-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-a]quinoxaline (IRFI 165) is the most potent compound in this series, having K(i)(A1) = 7.9 nM. It is also provided with a good A1 selectivity both versus A(2a) and A3 subtypes and was selected for further pharmacological studies.
