Evidence map›Paper›PMID 26889756›Full record

ArticleChemMedChem2016

Antineoplastic Isoflavonoids Derived from Intermediate ortho-Quinone Methides Generated from Mannich Bases.

Mykhaylo S Frasinyuk, Galyna P Mrug, Svitlana P Bondarenko, Volodymyr P Khilya, Vitaliy M Sviripa, Oleksandr A Syrotchuk, Wen Zhang, Xianfeng Cai, Michael V Fiandalo, James L Mohler and 2 more

Open access · greenAbstract read
In one paragraph

Article in ChemMedChem, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing papers in PubMed
3.8field-weighted citation impact, top 8% 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

9 citing papers in PubMed, 27 citations in OpenAlex.

  1. Review
  2. Article
  3. Review
  4. Article
  5. Article
  6. The Versatile and StrategicChemical reviews · 2024
    Review
  7. Article
  8. Mannich base-connected syntheses mediated byBeilstein journal of organic chemistry · 2018
    Review
  9. 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

12 authors at 6 institutions in 2 countries.

Mykhaylo S FrasinyukDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA. mykhaylo.frasinyuk@ukr.net.
Galyna P MrugDepartment of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, Kyiv, 02094, Ukraine.
Svitlana P BondarenkoDepartment of Chemistry, Taras Shevchenko Kyiv National University, Kyiv, 01601, Ukraine.
Volodymyr P KhilyaDepartment of Chemistry, Taras Shevchenko Kyiv National University, Kyiv, 01601, Ukraine.
Vitaliy M SviripaDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA.
Oleksandr A SyrotchukCentral Laboratory for Quality Control of Medicines and Medical Products, Kyiv, 04053, Ukraine.
Wen ZhangDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA.
Xianfeng CaiDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA.
Michael V FiandaloDepartment of Urology, Roswell Park Cancer Institute, Buffalo, NY, 14263, USA.
James L MohlerDepartment of Urology, Roswell Park Cancer Institute, Buffalo, NY, 14263, USA.
Chunming LiuDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA.
David S WattDepartment of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY, 40536-0596, USA. dwatt@uky.edu.
University of Kentucky · USInstitute of Bioorganic Chemistry and Petrochemistry V.P. Kukhar · UAMarkey Cancer Center · USRoswell Park Comprehensive Cancer Center · USTaras Shevchenko National University of Kyiv · UAKyiv Medical University · UA

Funding

Tumor stem cells in androgen independent prostate cancerP01CA077739 · NCI · UNIV OF NORTH CAROLINA CHAPEL HILL · PI MOHLER, JAMES L · 1998 to 2014
$16.8M
Protein CoreP30GM110787 · NIGMS · UNIVERSITY OF KENTUCKY · PI WHITEHEART, SIDNEY WALDO · 2014 to 2018
$5.7M
Novel resveratrol analogs and colorectal cancer treatmentR01CA172379 · NCI · UNIVERSITY OF KENTUCKY · PI LIU, CHUNMING · 2013 to 2017
$1.5M
Mechanisms of Wnt/beta-catenin inhibition by resveratrol and its derivativesR21CA139359 · NCI · UNIVERSITY OF KENTUCKY · PI LIU, CHUNMING · 2011 to 2012
$355k
Beta-catenin regulation by tumor suppressor APCR21CA112007 · NCI · UNIVERSITY OF TEXAS MEDICAL BR GALVESTON · PI LIU, CHUNMING · 2005 to 2006
$269k
NCI NIH HHS CA172379NCI NIH HHS P01 CA077739NCI NIH HHS P01 CA77739NCI NIH HHS R01 CA172379NCI NIH HHS R21 CA112007NCI NIH HHS R21 CA139359NIGMS NIH HHS P30 GM110787
6 · The paper itself

Abstract

The regioselective condensations of various 7-hydroxyisoflavonoids with bis(N,N-dimethylamino)methane in a Mannich reaction provided C-8 N,N-dimethylaminomethyl-substituted isoflavonoids in good yield. Similar condensations of 7-hydroxy-8-methylisoflavonoids led to the C-6-substituted analogs. Thermal eliminations of dimethylamine from these C-6 or C-8 N,N-dimethylaminomethyl-substituted isoflavonoids generated ortho-quinone methide intermediates within isoflavonoid frameworks for the first time. Despite other potential competing outcomes, these ortho-quinone methide intermediates trapped dienophiles including 2,3-dihydrofuran, 3,4-dihydro-2H-pyran, 3-(N,N-dimethylamino)-5,5-dimethyl-2-cyclohexen-1-one, 1-morpholinocyclopentene, and 1-morpholinocyclohexene to give various inverse electron-demand Diels-Alder adducts. Several adducts derived from 8-N,N-dimethylaminomethyl-substituted isoflavonoids displayed good activity in the 1-10 μm concentration range in an in vitro proliferation assay using the PC-3 prostate cancer cell line.

Indexed as

Antineoplastic AgentsCell Line, TumorCell ProliferationCycloaddition ReactionHumansIsoflavonesMannich BasesPyransStereoisomerismXanthenesAntineoplastic AgentsIsoflavonesMannich BasesPyransXanthenesinverse electron-demand Diels-Alder reactionisoflavonoidsMannich reactionsortho-quinone methidesprostate cancer PC-3 cell line

Identifiers

PMID26889756
PMCPMC4818953
OpenAlexW2277272100

What OpenQuestion holds

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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.