Synthesis of Indoloquinolines: An Intramolecular Cyclization Leading to Advanced Perophoramidine-Relevant Intermediates.

Craig A Johnston, David B Cordes, Tomas Lebl, Alexandra M Z Slawin, Nicholas J Westwood

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing 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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

5 authors.

Craig A JohnstonSchool of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK.

David B CordesSchool of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK.ORCID 0000-0002-5366-9168

Tomas LeblSchool of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK.

Alexandra M Z SlawinSchool of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK.ORCID 0000-0002-9527-6418

Nicholas J WestwoodSchool of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, North Haugh, St. Andrews KY16 9ST, UK.ORCID 0000-0003-0630-0138

Funding

Engineering and Physical Sciences Research Council PhD studentship for CAJ

6 · The paper itself

Abstract

The bioactive natural product perophoramidine has proved a challenging synthetic target. An alternative route to its indolo[2,3-b]quinolone core structure involving a N-chlorosuccinimde-mediated intramolecular cyclization reaction is reported. Attempts to progress towards the natural product are also discussed with an unexpected deep-seated rearrangement of the core structure occurring during an attempted iodoetherification reaction. X-ray crystallographic analysis provides important analytical confirmation of assigned structures.

Indexed as

Biological ProductsCrystallography, X-RayCyclizationHeterocyclic Compounds, 4 or More RingsHydrocarbons, HalogenatedMolecular StructureQuinolinesStereoisomerismBiological ProductsHeterocyclic Compounds, 4 or More RingsHydrocarbons, HalogenatedperophoramidineQuinolinesClaisen rearrangementindoloquinolineintramolecular cyclizationnatural productperophoramidineX-ray structure

Identifiers

PMID34641583

DOI10.3390/molecules26196039

PMCPMC8513048

What OpenQuestion holds

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LicenceCC BY

Read underepoch 390

Registered trials

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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.