ArticleChemical biology & drug design2009
A forward chemical screen using zebrafish embryos with novel 2-substituted 2H-chromene derivatives.
Article in Chemical biology & drug design, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 34 citations in OpenAlex.
- Development of a New Methodology for Dearomative Borylation of Coumarins and Chromenes and Its Applications to Synthesize Boron-Containing Retinoids.Molecules (Basel, Switzerland) · 2023Article
- Synthesis of a boron-containing amidoxime reagent and its application to synthesize functionalized oxadiazole and quinazolinone derivatives.Tetrahedron letters · 2022Article
- Small molecules targeting LapB protein prevent Listeria attachment to catfish muscle.PloS one · 2017Article
- Chemical screening in zebrafish for novel biological and therapeutic discovery.Methods in cell biology · 2017Review
- 15 years of zebrafish chemical screening.Current opinion in chemical biology · 2015Article
- Metalloradical approach to 2H-chromenes.Journal of the American Chemical Society · 2014Article
- Gold(I)-catalyzed hydroarylation reaction of aryl (3-iodoprop-2-yn-1-yl) ethers: synthesis of 3-iodo-2H-chromene derivatives.Beilstein journal of organic chemistry · 2013Article
- Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs.Tetrahedron letters · 2012Article
- Design, synthesis and biological study of pinacolyl boronate-substituted stilbenes as novel lipogenic inhibitors.Bioorganic & medicinal chemistry letters · 2011Article
- Article
- Small molecule screening in zebrafish.Journal of cardiovascular translational research · 2010Review
- Small molecule screening in zebrafish: an in vivo approach to identifying new chemical tools and drug leads.Cell communication and signaling : CCS · 2010Article
- Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.Tetrahedron letters · 2010Article
- Design and synthesis of novel pinacolylboronate containing combretastatin 'antimitotic agent' analogues.Tetrahedron letters · 2009Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
We synthesized 2-substituted 2H-chromene derivatives from salicylaldehyde using potassium vinylic borates in the presence of secondary amines. Our goal was to generate novel compounds that might modulate transforming growth factor-beta signaling, based on limited rational design. Potassium vinyl trifluoroborates react with salicylaldehydes at 80 degrees C in the presence of a secondary amine and produce 2-substituted 2H-chromene derivatives with a 70-90% yield. A small library of these compounds, predicted to potentially interact with transforming growth factor-beta receptors, was screened for bioactivity in living zebrafish embryos. We found that the related compounds differentially affect development, and demonstrate one compound that produces severe body axis alterations in early embryogenesis and at lower doses affects specifically cardiovascular development. This compound modulates specifically a Smad-independent transforming growth factor-beta-regulated mitogen-activated protein kinase pathway, namely p-SAPK/JNK. These compounds, as suggested by our biological assays, may prove useful to manipulate developmental programs and develop therapeutic tools.
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Registered trials
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.