ArticleJournal of natural products2011
Opioid receptor probes derived from cycloaddition of the hallucinogen natural product salvinorin A.
Article in Journal of natural products, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Solving an Old Puzzle: Elucidation and Evaluation of the Binding Mode of Salvinorin A at the Kappa Opioid Receptor.Molecules (Basel, Switzerland) · 2023Article
- Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.Biochemistry · 2021Review
- Cutting-Edge Search for Safer Opioid Pain Relief: Retrospective Review of Salvinorin A and Its Analogs.Frontiers in psychiatry · 2019Review
- A review of salvinorin analogs and their kappa-opioid receptor activity.Bioorganic & medicinal chemistry letters · 2018Review
- Dynamic Strategic Bond Analysis Yields a Ten-Step Synthesis of 20-nor-Salvinorin A, a Potent κ-OR Agonist.ACS central science · 2017Article
- Modular Approach to pseudo-Neoclerodanes as Designer κ-Opioid Ligands.Organic letters · 2017Article
- The C-2 derivatives of salvinorin A, ethoxymethyl ether Sal B and β-tetrahydropyran Sal B, have anti-cocaine properties with minimal side effects.Psychopharmacology · 2017Article
- Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor.European journal of medicinal chemistry · 2014Article
- Stilbenes as κ-selective, non-nitrogenous opioid receptor antagonists.Journal of natural products · 2014Article
- Salvinorin A analogs and other κ-opioid receptor compounds as treatments for cocaine abuse.Advances in pharmacology (San Diego, Calif.) · 2014Review
- Kappa-opioid receptor-selective dicarboxylic ester-derived salvinorin A ligands.Bioorganic & medicinal chemistry letters · 2013Article
- Neoclerodanes as atypical opioid receptor ligands.Journal of medicinal chemistry · 2013Review
- Semisynthetic neoclerodanes as kappa opioid receptor probes.Bioorganic & medicinal chemistry · 2012Article
- Potential Drug Abuse Therapeutics Derived from the Hallucinogenic Natural Product Salvinorin A.MedChemComm · 2011Article
Corrections and comments
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Authors and funding
7 authors.
Funding
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 oxanorbornadiene system possessed by the cycloadducts to a planar phenyl ring system. Although dimethyl- and diethylcarboxylate analogues 5 and 6 retain some affinity and selectivity for KOP receptors and are full agonists, their aromatized counterparts 13 and 14 have reduced affinity for KOP receptors. The methods developed herein signify a novel approach toward rapidly probing the structure-activity relationships of furan-containing natural products.
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