Evidence map›Paper›PMID 28433513›Full record

ArticleBioorganic & medicinal chemistry2017

Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities.

John T Gupton, Scott Yeudall, Nakul Telang, Megan Hoerrner, Ellis Huff, Evan Crawford, Katie Lounsbury, Michael Kimmel, William Curry, Andrew Harrison and 11 more

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Bioorganic & medicinal chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
–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

1 citing paper in PubMed.

  1. 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

21 authors.

John T GuptonDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA. Electronic address: jgupton@richmond.edu.
Scott YeudallDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Nakul TelangDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Megan HoerrnerDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Ellis HuffDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Evan CrawfordDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Katie LounsburyDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Michael KimmelDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
William CurryDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Andrew HarrisonDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Wen JuekunDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Alex ShimozonoDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Joe OrtolaniDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Kristin LescalleetDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Jon PattesonDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Veronica Moore-StollDepartment of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Cristina C RohenaDepartment of Pharmacology and Cancer Therapy & Research Center, University of Texas Health Science Center at San Antonio, San Antonio, TX 78229, USA.
Susan L MooberryDepartment of Pharmacology and Cancer Therapy & Research Center, University of Texas Health Science Center at San Antonio, San Antonio, TX 78229, USA.
Ahmad J ObaidullahDepartment of Medicinal Chemistry & Institute of Structural Biology, Drug Discovery and Development, Virginia Commonwealth University, Richmond, VA 23298, USA.
Glen E KelloggDepartment of Medicinal Chemistry & Institute of Structural Biology, Drug Discovery and Development, Virginia Commonwealth University, Richmond, VA 23298, USA.
James A SikorskiChemistry and Drug Discovery, Chesterfield, MO 63005, USA.

Funding

The Synthesis and Biological Evaluation of Pyrrole Containing Marine Natural ProdR15CA067236 · NCI · UNIVERSITY OF RICHMOND · PI GUPTON, JOHN T. · 1996 to 2012
$882k
NCI NIH HHS R15 CA067236
6 · The paper itself

Abstract

New microtubule depolymerizing agents with potent cytotoxic activities have been prepared with a 5-cyano or 5-oximino group attached to a pyrrole core. The utilization of ortho activation of a bromopyrrole ester to facilitate successful Suzuki-Miyaura cross-coupling reactions was a key aspect of the synthetic methodology. This strategy allows for control of regiochemistry with the attachment of four completely different groups at the 2, 3, 4 and 5 positions of the pyrrole scaffold. Biological evaluations and molecular modeling studies are reported for these examples.

Indexed as

AnimalsAntineoplastic AgentsCattleCell Line, TumorCell ProliferationCell SurvivalHalogenationHumansMicrotubulesMolecular Docking SimulationNeoplasmsPyrrolesRatsAntineoplastic AgentsPyrrolesCytotoxic activityMarine natural productsMicrotubule inhibitorsPyrroleSuzuki-Miyaura cross-coupling

Identifiers

PMID28433513
PMCPMC5517042

What OpenQuestion holds

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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.