Evidence map›Paper›PMID 37556912›Full record

ArticleBioorganic & medicinal chemistry2023

Structure Guided Design, Synthesis, and Biological Evaluation of Oxetane-Containing Indole Analogues.

Wen Ren, Rebecca Vairin, Jacob D Ward, Ricardo Francis, Jenny VanNatta, Ruoli Bai, Pouguiniseli E Tankoano, Yuling Deng, Ernest Hamel, Mary Lynn Trawick and 1 more

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

Article in Bioorganic & medicinal chemistry, 2023. 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
0.4field-weighted citation impact, top 42% 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

0 citing papers in PubMed, 3 citations in OpenAlex.

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

11 authors at 2 institutions in 1 country.

Wen RenDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Rebecca VairinDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Jacob D WardDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Ricardo FrancisDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Jenny VanNattaDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Ruoli BaiMolecular Pharmacology Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick National Laboratory for Cancer Research, National Institutes of Health, Frederick, MD 21702, United States.
Pouguiniseli E TankoanoDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Yuling DengDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Ernest HamelMolecular Pharmacology Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick National Laboratory for Cancer Research, National Institutes of Health, Frederick, MD 21702, United States.
Mary Lynn TrawickDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States.
Kevin G PinneyDepartment of Chemistry and Biochemistry, Baylor University, One Bear Place, No. 97348, Waco, TX 76798-7348, United States. Electronic address: Kevin_Pinney@baylor.edu.
Baylor University · USNational Institutes of Health · US

Funding

Vascular image-guided optimization of response (VIGOR) to therapy in kidney cancerR01CA244579 · NCI · UT SOUTHWESTERN MEDICAL CENTER · PI LIU, LI, PINNEY, KEVIN G. · 2020 to 2024
$2.4M
Novel Protein Engineered Drug Conjugates Targeting Phosphatidylserine for the Treatment of Breast CancerR01CA238624 · NCI · BAYLOR UNIVERSITY · PI BREKKEN, ROLF A, PINNEY, KEVIN G. · 2020 to 2023
$1.9M
CCR NIH HHS HHSN261200800001CNCI NIH HHS HHSN261200800001ENCI NIH HHS R01 CA238624NCI NIH HHS R01 CA244579
6 · The paper itself

Abstract

The oxetane functional group offers a variety of potential advantages when incorporated within appropriate therapeutic agents as a ketone surrogate. OXi8006, a 2-aryl-3-aroyl-indole analogue, functions as a small-molecule inhibitor of tubulin polymerization that has a dual mechanism of action as both an antiproliferative agent and a tumor-selective vascular disrupting agent. Replacement of the bridging ketone moiety in OXi8006 with an oxetane functional group has expanded structure activity relationship (SAR) knowledge and provided insights regarding oxetane incorporation within this class of molecules. A new synthetic method using an oxetane-containing tertiary alcohol subjected to Lewis acid catalyzed conditions led to successful Friedel-Crafts alkylation and yielded fourteen new oxetane-containing indole-based molecules. This synthetic approach represents the first method to successfully install an oxetane ring at the 3-position of a 2-aryl-indole system. Several analogues showed potent cytotoxicity (micromolar GI

Indexed as

Antineoplastic AgentsCell Line, TumorCell ProliferationColchicineDrug Screening Assays, AntitumorEthers, CyclicHumansIndolesMolecular Docking SimulationMolecular StructureStructure-Activity RelationshipTubulinTubulin ModulatorsAntineoplastic AgentsColchicineEthers, CyclicIndolesoxetaneTubulinTubulin ModulatorsFriedel-Crafts alkylationInhibition of tubulin polymerizationOxetane

Identifiers

PMID37556912
PMCPMC10848874
OpenAlexW4382518262

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.