Synthesis of (2

Adrian O Dukes, Pathum M Weerawarna, Allison N Devitt, Richard B Silverman

Abstract read

In one paragraph

Article in The Journal of organic chemistry, 2024. 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

4 authors.

Adrian O DukesDepartments of Chemistry and Molecular Biosciences, Chemistry of Life Processes Institute, and Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208, United States.

Pathum M WeerawarnaDivision of Clinical Pharmacology, School of Medicine, Indiana University, Indianapolis, Indiana 46202, United States.ORCID 0000-0002-9859-0787

Allison N DevittDepartments of Chemistry and Molecular Biosciences, Chemistry of Life Processes Institute, and Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208, United States.ORCID 0000-0003-2816-7120

Richard B SilvermanDepartments of Chemistry and Molecular Biosciences, Chemistry of Life Processes Institute, and Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208, United States.ORCID 0000-0001-9034-1084

Funding

Ornithine Aminotransferase Inactivation, a New Approach for Treatment of CancersR01CA260250 · NCI · NORTHWESTERN UNIVERSITY · PI RICHARD B SILVERMAN · 2021 to 2026

$2.3M

NCI NIH HHS R01 CA260250

6 · The paper itself

Abstract

Inhibition of human ornithine aminotransferase interferes with glutamine and proline metabolism in hepatocellular carcinoma, depriving tumors of essential nutrients. A proposed mechanism-based inhibitor containing a bicyclo[3.1.1]heptanol warhead is reported herein. The proposed inactivation mechanism involves a novel α-iminol rearrangement. The synthesis of the proposed inhibitor features an asymmetric intramolecular Mannich reaction, utilizing a chiral sulfinamide. This study presents a novel approach toward the synthesis of functionalized bicyclo[3.1.1]heptanes and highlights an underutilized method to access enantiopure exocyclic amines.

Indexed as

Carboxylic AcidsBridged Bicyclo CompoundsHumansMolecular StructureStereoisomerismBridged Bicyclo CompoundsCarboxylic Acids

Identifiers

PMID38857432

DOI10.1021/acs.joc.4c00781

PMCPMC11418922

What OpenQuestion holds

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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.