Structure-activity relationships of dermorphin analogues containing chiral piperazin-2-one and piperazine derivatives.
Chem Pharm Bull (Tokyo)
; 44(4): 856-9, 1996 Apr.
Article
em En
| MEDLINE
| ID: mdl-8681417
ABSTRACT
The amide and ester carbonyl groups of four piperazin-2-one derivatives (N,N'-ethylene-bridged dipeptide ethyl esters) constructed from (R)- or (S)-phenylalanine and glycine were reduced with borane-tetrahydrofuran complex to produce the corresponding piperazine derivatives in 70-80% yields. These piperazin-2-one or piperazine derivatives were used as the carboxyl-terminal residues of eight dermorphin analogues (H-tyrosyl-D-alanyl-piperazine derivatives were used as the carboxyl-terminal residues of eight dermorphin analogues (H-tyrosyl-D-alanyl-piperazin-2-one or piperazine derivatives) whose opiate activities were examined in vitro by use of the guinea pig ileum and the mouse vas deferens assays. It was found in the guinea pig ileum assay that the configuration of pheylalanine and the replacement of the piperazin-2-one ring with a piperazine ring are important for enhancing or reducing the opiate activities of these analogues.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oligopeptídeos
/
Piperazinas
/
Analgésicos Opioides
Limite:
Animals
Idioma:
En
Revista:
Chem Pharm Bull (Tokyo)
Ano de publicação:
1996
Tipo de documento:
Article