Opioid receptor probes derived from cycloaddition of the hallucinogen natural product salvinorin A.

ABSTRACT: As part of our continuing efforts toward more fully understanding the structure-activity relationships of the neoclerodane diterpene salvinorin A, we report the synthesis and biological characterization of unique cycloadducts through [4+2] Diels-Alder cycloaddition. Microwave-assisted methods were developed and successfully employed, aiding in functionalizing the chemically sensitive salvinorin A scaffold. This demonstrates the first reported results for both cycloaddition of the furan ring and functionalization via microwave-assisted methodology of the salvinorin A skeleton. The cycloadducts yielded herein introduce electron-withdrawing substituents and bulky aromatic groups into the C-12 position. Kappa opioid (KOP) receptor space was explored through aromatization of the bent oxanorborn

SUBMITTER: Lozama A 

PROVIDER: S-EPMC3081938 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature