ArticleChemMedChem2016
Synthesis and Antiangiogenic Properties of Tetrafluorophthalimido and Tetrafluorobenzamido Barbituric Acids.
Article in ChemMedChem, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Fluorinated Aminopiperidones as Non-Glutarimide Thalidomide Analogs: Stereodivergent Synthesis and Validation.ChemMedChem · 2026Article
- The Multifaceted Legacy of Thalidomide: Chemistry and Biology Driving Modern Drug Design.ChemMedChem · 2026Review
- Revisiting the antiangiogenic mechanisms of fluorinated thalidomide derivatives.Bioorganic & medicinal chemistry letters · 2024Article
- Leveraging Ligand Affinity and Properties: Discovery of Novel Benzamide-Type Cereblon Binders for the Design of PROTACs.Journal of medicinal chemistry · 2023Article
- On the correlation of cereblon binding, fluorination and antiangiogenic properties of immunomodulatory drugs.Biochemical and biophysical research communications · 2021Article
- Antiangiogenic Activity and in Silico Cereblon Binding Analysis of Novel Thalidomide Analogs.Molecules (Basel, Switzerland) · 2020Article
- Synthesis, Structural Characterization, and Antiangiogenic Activity of Polyfluorinated Benzamides.ChemMedChem · 2018Article
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Authors and funding
7 authors.
Funding
Abstract
The development of novel thalidomide derivatives as immunomodulatory and anti-angiogenic agents has revived over the last two decades. Herein we report the design and synthesis of three chemotypes of barbituric acids derived from the thalidomide structure: phthalimido-, tetrafluorophthalimido-, and tetrafluorobenzamidobarbituric acids. The latter were obtained by a new tandem reaction, including a ring opening and a decarboxylation of the fluorine-activated phthalamic acid intermediates. Thirty compounds of the three chemotypes were evaluated for their anti-angiogenic properties in an ex vivo assay by measuring the decrease in microvessel outgrowth in rat aortic ring explants. Tetrafluorination of the phthalimide moiety in tetrafluorophthalimidobarbituric acids was essential, as all of the nonfluorinated counterparts lost anti-angiogenic activity. An opening of the five-membered ring and the accompanying increased conformational freedom, in case of the corresponding tetrafluorobenzamidobarbituric acids, was well tolerated. Their activity was retained, although their molecular structures differ in torsional flexibility and possible hydrogen-bond networking, as revealed by comparative X-ray crystallographic analyses.
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Registered trials
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