Abstract
Since most of the reported adenosine receptor antagonists are 2-(hetero)aryl-substituted tricyclic heteroaromatic derivatives, in the present study we report the synthesis and the biological evaluation of a new set of 4-amino-1,2,4-triazolo[1,5-a]quinoxalines containing at position-2 an ethyl carboxylate group or a hydrogen atom. The structure-activity relationships on these compounds were in accordance with those of a previously reported series of analogous size and shape, thus suggesting a similar A(1)-binding mode. In particular, the binding data indicate that alkylation of the 4-amino group of these derivatives lead to potent A(1)-receptor antagonists. Moreover, as new results, this study has pointed out that the ethyl 2-carboxylate group can advantageously replace the 2-(hetero)aryl ring of previously reported triazoloquinoxaline derivatives, affording an ameliorated interaction with the A(1)-receptor subtype.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenosine / analogs & derivatives
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Adenosine / pharmacology
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Adenosine A1 Receptor Antagonists
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Adenosine A2 Receptor Antagonists
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Adenosine A3 Receptor Antagonists
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Animals
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Binding, Competitive / drug effects
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CHO Cells
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Cattle
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Cerebral Cortex / drug effects
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Cerebral Cortex / metabolism
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Cricetinae
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Humans
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In Vitro Techniques
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Indicators and Reagents
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Kinetics
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Magnetic Resonance Spectroscopy
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Neostriatum / metabolism
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Purinergic P1 Receptor Antagonists*
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Quinoxalines / chemical synthesis*
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Quinoxalines / pharmacology*
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Spectrophotometry, Infrared
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Structure-Activity Relationship
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Triazoles / chemical synthesis*
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Triazoles / pharmacology*
Substances
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1,2,4-Triazolo(1,5-a)quinoxaline
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Adenosine A1 Receptor Antagonists
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Adenosine A2 Receptor Antagonists
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Adenosine A3 Receptor Antagonists
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Indicators and Reagents
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Purinergic P1 Receptor Antagonists
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Quinoxalines
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Triazoles
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N(6)-cyclohexyladenosine
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Adenosine