Evidence map›Paper›PMID 31147103›Full record

ArticleBioorganic & medicinal chemistry letters2019

Determining the necessity of phenyl ring π-character in warfarin.

Hui Xing, Sevan D Houston, Xuejie Chen, Da-Yun Jin, G Paul Savage, Jian-Ke Tie, Craig M Williams

Open access · greenAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Bioorganic & medicinal chemistry letters, 2019. 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
2.1field-weighted citation impact, top 14% 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

1 citing paper in PubMed, 13 citations in OpenAlex.

  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

7 authors at 3 institutions in 2 countries.

Hui XingSchool of Chemistry and Molecular Biosciences, University of Queensland, Brisbane 4072, Queensland, Australia.
Sevan D HoustonSchool of Chemistry and Molecular Biosciences, University of Queensland, Brisbane 4072, Queensland, Australia.
Xuejie ChenDepartment of Biology, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Da-Yun JinDepartment of Biology, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
G Paul SavageCSIRO Manufacturing, Ian Wark Laboratory, Melbourne 3168, Victoria, Australia.
Jian-Ke TieDepartment of Biology, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.
Craig M WilliamsSchool of Chemistry and Molecular Biosciences, University of Queensland, Brisbane 4072, Queensland, Australia. Electronic address: c.williams3@uq.edu.au.
University of North Carolina at Chapel Hill · USUniversity of Queensland · AUCSIRO Manufacturing · AU

Funding

Characterization of enzymes in the vitamin K cycleR01HL131690 · NHLBI · UNIV OF NORTH CAROLINA CHAPEL HILL · PI STAFFORD, DARREL W, TIE, JIANKE · 2016 to 2023
$4.0M
NHLBI NIH HHS R01 HL131690
6 · The paper itself

Abstract

Despite the difficulty in administering a safe dose regimen and reports of emerging resistance, warfarin (1) remains the most widely-used oral anticoagulant for the prevention and treatment of thrombosis in humans globally. Systematic substitution of the warfarin phenyl ring with either 1,3,5,7-cyclooctatetraene (COT) (2), cubane (3), cyclohexane (4) or cyclooctane (5) and subsequent evaluation against the target enzyme, vitamin K epoxide reductase (VKOR), facilitated interrogation of both steric and electronic properties of the phenyl pharmacophore. The tolerance of VKOR to further functional group modification (carboxylate 14, PTAD adduct 15) was also investigated. The results demonstrate the importance of both annulene conferred π-interactions and ring size in the activity of warfarin.

Indexed as

AnticoagulantsHumansWarfarinAnticoagulantsWarfarinCyclohexaneCyclooctaneVKORWarfarinπ-Interaction

Identifiers

PMID31147103
PMCPMC7874505
OpenAlexW2945082287

What OpenQuestion holds

Textmetadata
LicenceTDM
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.