Evidence map›Paper›PMID 28376298›Full record

ArticleJournal of medicinal chemistry2017

Addressing Structural Flexibility at the A-Ring on Salvinorin A: Discovery of a Potent Kappa-Opioid Agonist with Enhanced Metabolic Stability.

Alexander M Sherwood, Rachel Saylor Crowley, Kelly F Paton, Andrew Biggerstaff, Benjamin Neuenswander, Victor W Day, Bronwyn M Kivell, Thomas E Prisinzano

Abstract read
In one paragraph

Article in Journal of medicinal chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers, 1 of them a synthesis that pooled it.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed, 1 pooled it
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

16 citing papers in PubMed, 1 synthesis or guideline pooled it.

  1. Pooled it
  2. Article
  3. Article
  4. A Protecting-Group-Free Synthesis of (-)-Salvinorin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021
    Article
  5. Review
  6. Review
  7. Review
  8. Strategies for DevelopingThe Journal of pharmacology and experimental therapeutics · 2020
    Review
  9. Article
  10. Review
  11. Review
  12. Article
  13. A review of salvinorin analogs and their kappa-opioid receptor activity.Bioorganic & medicinal chemistry letters · 2018
    Review
  14. Article
  15. Article
  16. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

8 authors.

Alexander M SherwoodDepartment of Medicinal Chemistry, School of Pharmacy, The University of Kansas , Lawrence, Kansas 66045, United States.
Rachel Saylor CrowleyDepartment of Medicinal Chemistry, School of Pharmacy, The University of Kansas , Lawrence, Kansas 66045, United States.
Kelly F PatonSchool of Biological Sciences, Centre for Biodiscovery, Victoria University of Wellington , Wellington 6012, New Zealand.
Andrew BiggerstaffSchool of Biological Sciences, Centre for Biodiscovery, Victoria University of Wellington , Wellington 6012, New Zealand.
Benjamin NeuenswanderDepartment of Medicinal Chemistry, School of Pharmacy, The University of Kansas , Lawrence, Kansas 66045, United States.
Victor W DayDepartment of Chemistry, The University of Kansas , Lawrence, Kansas 66045, United States.
Bronwyn M KivellSchool of Biological Sciences, Centre for Biodiscovery, Victoria University of Wellington , Wellington 6012, New Zealand.
Thomas E PrisinzanoDepartment of Medicinal Chemistry, School of Pharmacy, The University of Kansas , Lawrence, Kansas 66045, United States.ORCID 0000-0002-0649-8052

Funding

Investigation of Neoclerodanes as Novel Opioid LigandsR01DA018151 · NIDA · UNIVERSITY OF KENTUCKY · PI PRISINZANO, THOMAS EDWARD · 2005 to 2020
$5.7M
TRAINING GRANT IN DYNAMIC ASPECTS OF CHEMICAL BIOLOGYT32GM008545 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI LAMB, AUDREY L · 1994 to 2019
$4.9M
Legacy continuation of the KU CMLD MissionR24GM111385 · NIGMS · UNIVERSITY OF KANSAS LAWRENCE · PI PRISINZANO, THOMAS EDWARD · 2014 to 2016
$1.5M
Avance II 500 High Performance Digital NMR Spectrometer SystemS10RR024664 · NCRR · UNIVERSITY OF KANSAS LAWRENCE · PI VANDERVELDE, DAVID G · 2007 to 2007
$468k
NCRR NIH HHS S10 RR024664NIDA NIH HHS R01 DA018151NIGMS NIH HHS R24 GM111385NIGMS NIH HHS T32 GM008545
6 · The paper itself

Abstract

Previous structure-activity studies on the neoclerodane diterpenoid salvinorin A have demonstrated the importance of the acetoxy functionality on the A-ring in its activity as a κ-opioid receptor agonist. Few studies have focused on understanding the role of conformation in these interactions. Herein we describe the synthesis and evaluation of both flexible and conformationally restricted compounds derived from salvinorin A. One such compound, spirobutyrolactone 14, was synthesized in a single step from salvinorin B and had similar potency and selectivity to salvinorin A (EC

Indexed as

AnalgesicsAnimalsChromatography, High Pressure LiquidCrystallography, X-RayDiterpenes, ClerodaneLigandsMaleMass SpectrometryMicrosomesReceptors, Opioid, kappaSpectrophotometry, UltravioletStructure-Activity RelationshipAnalgesicsDiterpenes, ClerodaneLigandsReceptors, Opioid, kappasalvinorin A

Identifiers

PMID28376298
PMCPMC5546011

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Registered trials

None linked

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.