1-Phenylpyrazolo[3,4-d]pyrimidines; structure-ac:tivity relationships for C6 substituents at A1 and A2A adenosine receptors.
Bioorg Med Chem
; 8(11): 2581-90, 2000 Nov.
Article
en En
| MEDLINE
| ID: mdl-11092543
ABSTRACT
Substitution of I-phenylpyrazolo[3,4-d]pyrimidines at C6 with N-alkyl-2-thiopropionamide groups has resulted in a series of 18 compounds which have been evaluated for binding at A1 and A2A adenosine receptors. Introduction of an N-ethyl group gave increased affinity at both A1 and A2A receptors for the amino compound 7b compared to the primary amide 7a. An additional hydrophobic pocket exists for substituents on the amide. This pocket allows an N-ethyl group for increased affinity at both A1 and A2A receptors, allows larger alkyl groups at A2A receptors but not at A1 receptors and there is an H-bond interaction requiring one H-bond donor. Molecular modeling studies have also enabled a proposal of the amino acid residues involved in ligand binding at both the A1 and A2A receptors.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Pirimidinas
/
Receptores Purinérgicos P1
Límite:
Animals
/
Humans
Idioma:
En
Revista:
Bioorg Med Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2000
Tipo del documento:
Article
País de afiliación:
Australia