Abstract
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 (9 R)- 1 exhibited higher affinity than (9 S)- 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 (9 S)- 1 showed μ-selective and μ-, κ-selective binding, respectively.
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