1220796-69-9Relevant academic research and scientific papers
Synthesis and evaluation of opioid receptor-binding affinity of elaeocarpenine and its analogs
Kurasaki, Haruaki,Okamoto, Iwao,Morita, Nobuyoshi,Tamura, Osamu
scheme or table, p. 1601 - 1603 (2010/06/16)
Both enantiomers of elaeocarpenine (1) and its analogs, 21, 22, 25, and 27, were synthesized from bicyclic aldehydes 8-10 via a flexible route previously established for total synthesis of grandisines, and their binding affinities for μ-, κ- and δ-opioid receptor subtypes were evaluated. We found that (9R)-1 exhibited higher affinity than (9S)-1 for all the subtypes, but the enantiomers showed little subtype selectivity. Analogs 21 having a pyrrolizidine skeleton and 27 having a stemona-type skeleton in place of the indolizidine unit of (9S)-1 showed μ-selective and μ-, κ-selective binding, respectively.
