title: Synthesis of salvinorin A analogues as opioid receptor probes.
abstract: Several neoclerodanes, such as salvinorin A (1) and herkinorin (3), have recently been shown to possess opioid receptor activity in vitro and in vivo. To explore the structure-affinity relationships of this interesting class of compounds, we have synthesized a series of analogues from 1 isolated from Salvia divinorum. Here, we report the semisynthesis of neoclerodane diterpenes and their structure-affinity relationships at opioid receptors. This work will allow the further development of novel opioid receptor ligands.
authors.affiliation: Division of Medicinal & Natural Products Chemistry, College of Pharmacy, The University of Iowa, Iowa City, Iowa 52242, USA.
authors.forename: Kevin
authors.initials: K
authors.lastname: Tidgewell
authors.forename: Wayne W
authors.initials: WW
authors.lastname: Harding
authors.forename: Anthony
authors.initials: A
authors.lastname: Lozama
authors.forename: Howard
authors.initials: H
authors.lastname: Cobb
authors.forename: Kushal
authors.initials: K
authors.lastname: Shah
authors.forename: Pavitra
authors.initials: P
authors.lastname: Kannan
authors.forename: Christina M
authors.initials: CM
authors.lastname: Dersch
authors.forename: Damon
authors.initials: D
authors.lastname: Parrish
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Deschamps
authors.forename: Richard B
authors.initials: RB
authors.lastname: Rothman
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Prisinzano
mesh_terms: D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045785:Diterpenes, Clerodane; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D011957:Receptors, Opioid / Q000819:agonists*; D027544:Salvia / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D004224:Diterpenes; D045785:Diterpenes, Clerodane; D011957:Receptors, Opioid; C090499:salvinorin A