1160747-77-2Relevant academic research and scientific papers
Homologous piperazine-alcanols: Chiral pool synthesis and pharmacological evaluation
Holl, Ralph,Schepmann, Dirk,Wünsch, Bernhard
, p. 673 - 679 (2012)
Starting with the proteinogenic amino acids (S)-aspartate and (S)-glutamate the homologous piperazine-alcanols 3 and 4 were prepared in a five step synthesis. The diversity was introduced by N-1 alkylation of the piperazinediones 5 and 6 with various alkyl halides. Subsequent LiAlH 4 reduction of the dioxopiperazine-esters 7 and 8 provided the alcohols 3 and 4. The ethanol derivatives 3 show similar σ1 affinity as the methanol derivatives 2, but increased selectivity over the σ2 subtype. The corresponding propanol derivatives 4 are considerably less potent. A benzyl or dimethylallyl residue at N-1 appears to be optimal for high σ1 affinity.
