ArticleBioorganic & medicinal chemistry2012
Semisynthetic neoclerodanes as kappa opioid receptor probes.
Article in Bioorganic & medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
17 citing papers in PubMed, 35 citations in OpenAlex.
- Emerging Psychotropic Drug for the Treatment of Trigeminal Pain: Salvinorin A.Pharmaceuticals (Basel, Switzerland) · 2024Review
- Synthesis of (-)-Cotylenol, a 14-3-3 Molecular Glue Component.Journal of the American Chemical Society · 2023Article
- A Route to Potent, Selective, and Biased Salvinorin Chemical Space.ACS central science · 2023Article
- Solving an Old Puzzle: Elucidation and Evaluation of the Binding Mode of Salvinorin A at the Kappa Opioid Receptor.Molecules (Basel, Switzerland) · 2023Article
- A Protecting-Group-Free Synthesis of (-)-Salvinorin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- 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
- Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.ACS catalysis · 2018Article
- Clerodane diterpenes: sources, structures, and biological activities.Natural product reports · 2016Review
- Studies toward the Development of Antiproliferative Neoclerodanes from Salvinorin A.Journal of natural products · 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
- LC-MS/MS quantification of salvinorin A from biological fluids.Analytical methods : advancing methods and applications · 2013Article
- Palladium-catalyzed transformations of salvinorin A, a neoclerodane diterpene from Salvia divinorum.Organic letters · 2013Article
- 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
Corrections and comments
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Authors and funding
11 authors at 4 institutions in 1 country.
Funding
Abstract
Modification of the furan ring of salvinorin A (1), the main active component of Salvia divinorum, has resulted in novel neoclerodane diterpenes with opioid receptor affinity and activity. Conversion of the furan ring to an aldehyde at the C-12 position (5) has allowed for the synthesis of analogues with new carbon-carbon bonds at that position. Previous methods for forming these bonds, such as Grignard and Stille conditions, have met with limited success. We report a palladium catalyzed Liebeskind-Srogl cross-coupling reaction of a thioester and a boronic acid that occurs at neutral pH and ambient temperature to produce ketone analogs at C-12. To the best of our knowledge, this is the first reported usage of the Liebeskind-Srogl reaction to diversify a natural product scaffold. We also describe a one-step protocol for the conversion of 1 to 12-epi-1 (3) through microwave irradiation. Previously, this synthetically challenging process has required multiple steps. Additionally, we report in this study that alkene 9 and aromatic analogues 12, 19, 23, 25, and 26 were discovered to retain affinity and selectivity at kappa opioid receptors (KOP). Finally, we report that the furan-2-yl analog of 1 (31) has similar affinity to 1. Collectively, these findings suggest that different aromatic groups appended directly to the decalin core may be well tolerated by KOP receptors, and may generate further ligands with affinity and activity at KOP 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.