ArticleBioorganic & medicinal chemistry2009
Modification of the furan ring of salvinorin A: identification of a selective partial agonist at the kappa opioid receptor.
Article in Bioorganic & medicinal chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 43 citations in OpenAlex.
- Review
- From Plant to Chemistry: Sources of Active Opioid Antinociceptive Principles for Medicinal Chemistry and Drug Design.Molecules (Basel, Switzerland) · 2023Review
- The Kappa Opioid Receptor Agonist 16-Bromo Salvinorin A Has Anti-Cocaine Effects without Significant Effects on Locomotion, Food Reward, Learning and Memory, or Anxiety and Depressive-like Behaviors.Molecules (Basel, Switzerland) · 2023Article
- 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
- Evaluation of Biased and Balanced Salvinorin A Analogs in Preclinical Models of Pain.Frontiers in neuroscience · 2020Article
- 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
- Semisynthesis and Kappa-Opioid Receptor Activity of Derivatives of Columbin, a Furanolactone Diterpene.Journal of natural products · 2017Article
- Clerodane diterpenes: sources, structures, and biological activities.Natural product reports · 2016Review
- Relative Timing Between Kappa Opioid Receptor Activation and Cocaine Determines the Impact on Reward and Dopamine Release.Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2016Article
- Synthesis and κ-opioid receptor activity of furan-substituted salvinorin A analogues.Journal of medicinal chemistry · 2014Article
- Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity.Beilstein journal of organic chemistry · 2013Article
- Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.Organic letters · 2013Article
- Semisynthetic neoclerodanes as kappa opioid receptor probes.Bioorganic & medicinal chemistry · 2012Article
- Differential signaling properties at the kappa opioid receptor of 12-epi-salvinorin A and its analogues.Bioorganic & medicinal chemistry letters · 2012Article
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A.Pharmacological reviews · 2011Review
- Opioid receptor probes derived from cycloaddition of the hallucinogen natural product salvinorin A.Journal of natural products · 2011Article
- Synthesis and biological evaluation of C-2 halogenated analogs of salvinorin A.Bioorganic & medicinal chemistry letters · 2010Article
- General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates.Organic letters · 2010Article
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Authors and funding
8 authors at 3 institutions in 1 country.
Funding
Abstract
In an effort to find novel agents which selectively target the kappa opioid receptor (KOPR), we modified the furan ring of the highly potent and selective KOPR agonist salvinorin A. Introduction of small substituents at C-16 was well tolerated. 12-epi-Salvinorin A, synthesized in four steps from salvinorin A, was a selective partial agonist at the KOPR. No clear SAR patterns were observed for C-13 aryl ketones. Introducing a hydroxymethylene group between C-12 and the furan ring was tolerated. Small C-13 esters and ethers gave weak KOPR agonists, while all C-13 amides were inactive. Finally, substitution of oxadiazoles for the furan ring abolished affinity for the KOPR. None of the compounds displayed any KOPR antagonism or any affinity for mu or delta opioid receptors.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.