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Bioorg Chem ; 92: 103183, 2019 11.
Artigo em Inglês | MEDLINE | ID: mdl-31446240

RESUMO

Adenosine receptor antagonists are generally based on heterocyclic core structures presenting substituents of various volumes and chemical-physical profiles. Adenine and purine-based adenosine receptor antagonists have been reported in literature. In this work we combined various substituents in the 2, 6, and 8-positions of 9-ethylpurine to depict a structure-affinity relationship analysis at the human adenosine receptors. Compounds were rationally designed trough molecular modeling analysis and then synthesized and evaluated at radioligand binding studies at human adenosine receptors. The new compounds showed affinity for the human adenosine receptors, with some derivatives endowed with low nanomolar Ki data, in particular at the A2AAR subtype. The purine core proves to be a versatile core structure for the development of novel adenosine receptor antagonists with nanomolar affinity for these membrane proteins.


Assuntos
Antagonistas do Receptor A2 de Adenosina/síntese química , Antagonistas do Receptor A2 de Adenosina/metabolismo , Purinas/síntese química , Purinas/metabolismo , Receptor A2A de Adenosina/metabolismo , Sequência de Aminoácidos , Animais , Sítios de Ligação , Células CHO , Cricetulus , Humanos , Ligantes , Masculino , Modelos Moleculares , Estrutura Molecular , Ligação Proteica , Ensaio Radioligante , Ratos Wistar , Relação Estrutura-Atividade
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