Evidence map›Paper›PMID 31164645›Full record

ArticleNature communications2019

A synthesis strategy for tetracyclic terpenoids leads to agonists of ERβ.

Wan Shin Kim, Zachary A Shalit, Sidney M Nguyen, Emmalie Schoepke, Alan Eastman, Thomas P Burris, Arti B Gaur, Glenn C Micalizio

Open access · goldAbstract read
In one paragraph

Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.

0numbers the graph read from it
0cells of the map it votes in
20citing papers in PubMed
2.0field-weighted citation impact, top 13% of its field
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

20 citing papers in PubMed, 24 citations in OpenAlex.

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  17. From anOrganic letters · 2021
    Article
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  19. Article
  20. Diversity-oriented synthesis of 17-spirosteroids.Beilstein journal of organic chemistry · 2020
    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 at 2 institutions in 1 country.

Wan Shin KimDartmouth College, Department of Chemistry, Burke Laboratory, Hanover, NH, 03755, USA.ORCID http://orcid.org/0000-0001-7151-2992
Zachary A ShalitDartmouth College, Department of Chemistry, Burke Laboratory, Hanover, NH, 03755, USA.
Sidney M NguyenDartmouth College, Geisel School of Medicine, Department of Neurology, Lebanon, NH, 03756, USA.
Emmalie SchoepkeCenter for Clinical Pharmacology, Washington University School of Medicine and St. Louis College of Pharmacy, St. Louis, MO, 63110, USA.
Alan EastmanDartmouth College, Geisel School of Medicine, Department of Molecular and Systems Biology, Lebanon, NH, 03756, USA.
Thomas P BurrisCenter for Clinical Pharmacology, Washington University School of Medicine and St. Louis College of Pharmacy, St. Louis, MO, 63110, USA.
Arti B GaurDartmouth College, Geisel School of Medicine, Department of Neurology, Lebanon, NH, 03756, USA. arti.b.gaur@dartmouth.edu.
Glenn C MicalizioDartmouth College, Department of Chemistry, Burke Laboratory, Hanover, NH, 03755, USA. glenn.c.micalizio@dartmouth.edu.ORCID http://orcid.org/0000-0002-3408-5570
Dartmouth College · USUniversity of Health Sciences and Pharmacy · US

Funding

Stereoselective Synthesis via Metallacycle-Mediated Bond ConstructionR01GM080266 · NIGMS · YALE UNIVERSITY · PI MICALIZIO, GLENN C · 2007 to 2019
$4.8M
Pharmacological Sciences Training GrantT32GM008306 · NIGMS · SAINT LOUIS UNIVERSITY · PI EGAN, TERRANCE M, WALKER, JOHN K. · 1990 to 2020
$3.6M
NIGMS NIH HHS R01 GM080266NIGMS NIH HHS T32 GM008306U.S. Department of Health & Human Services | National Institutes of Health (NIH) GM080266
6 · The paper itself

Abstract

Natural product and natural product-like molecules continue to be important for the development of pharmaceutical agents, as molecules in this class play a vital role in the pipeline for new therapeutics. Among these, tetracyclic terpenoids are privileged, with >100 being FDA-approved drugs. Despite this significant pharmaceutical success, there remain considerable limitations to broad medicinal exploitation of the class due to lingering scientific challenges associated with compound availability. Here, we report a concise asymmetric route to forging natural and unnatural (enantiomeric) C19 and C20 tetracyclic terpenoid skeletons suitable to drive medicinal exploration. While efforts have been focused on establishing the chemical science, early investigations reveal that the emerging chemical technology can deliver compositions of matter that are potent and selective agonists of the estrogen receptor beta, and that are selectively cytotoxic in two different glioblastoma cell lines (U251 and U87).

Indexed as

Brain NeoplasmsGlioblastomaApoptosisCell Line, TumorCell SurvivalDrug DevelopmentEstrogen Receptor betaHumansNeural Stem CellsStereoisomerismTerpenesEstrogen Receptor betaTerpenes

Identifiers

PMID31164645
PMCPMC6547701
OpenAlexW2948684195

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

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.