Structure-property relationships of fluorinated carboxylic acid bioisosteres

Alle, Thibault; Joyasawal, Sipak; Oukoloff, Killian; Long, Keith; Owyang, Zachary; Francisco, Karol R; Cahard, Dominique; Huryn, Donna M.; Ballatore, Carlo

doi:10.1016/j.bmcl.2023.129363

Cited by 3 publications

(1 citation statement)

References 10 publications

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“…[6] Another interesting motif is the gem-difluoromethylene group, which is recently receiving great attention due to its bioisosteric behavior as carbonyl and alcohol functional groups. [7] Within the fluoro-pharmaceuticals bearing a trifluoromethyl group in their skeleton, important and representative moieties are the 1-hydroxy-2,2,2-trifluoroethyl and 2,2,2-trifluoroacetyl groups. These two functionalized trifluoromethylated entities are presented in several pharmaceuticals, such as Befloxatone (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Hydroxytrifluoroethylation and Trifluoroacetylation Reactions via SET Processes

Gallego‐Gamo,

Pleixats,

Gimbert‐Suriñach

et al. 2024

Chemistry A European J

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Hydroxytrifluoroethyl and trifluoroacetyl groups are of utmost importance in biologically active compounds, but methods to tether these motifs to organic architectures have been limited. Typically, the preparation of these compounds relied on the use of strong bases or multistep routes. The renaissance of radical chemistry in photocatalytic, transition metal mediated, and hydrogen atom transfer (HAT) processes have allowed the installation of these medicinally relevant fluorinated motifs. This review provides an overview of the methods available for the direct synthesis of hydroxytrifluoroethyl‐ and trifluoroacetyl‐derived compounds governed by single‐electron transfer processes.

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Section: Introductionmentioning

confidence: 99%

Hydroxytrifluoroethylation and Trifluoroacetylation Reactions via SET Processes

Gallego‐Gamo,

Pleixats,

Gimbert‐Suriñach

et al. 2024

Chemistry A European J

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Bioisosterism in drug discovery

Chatzopoulou

2024

Bioorganic & Medicinal Chemistry

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The Role of Small Molecules Containing Fluorine Atoms in Medicine and Imaging Applications

Henary,

Casa,

Dost

et al. 2024

Pharmaceuticals

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The fluorine atom possesses many intrinsic properties that can be beneficial when incorporated into small molecules. These properties include the atom’s size, electronegativity, and ability to block metabolic oxidation sites. Substituents that feature fluorine and fluorine-containing groups are currently prevalent in drugs that lower cholesterol, relieve asthma, and treat anxiety disorders, as well as improve the chemical properties of various medications and imaging agents. The dye scaffolds (fluorescein/rhodamine, coumarin, BODIPY, carbocyanine, and squaraine dyes) reported will address the incorporation of the fluorine atom in the scaffold and the contribution it provides to its application as an imaging agent. It is also important to recognize radiolabeled fluorine atoms used for PET imaging in the early detection of diseases. This review will discuss the many benefits of incorporating fluorine atoms into small molecules and give examples of fluorinated molecules used in the pharmaceutical industry and imaging techniques.

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Structure-property relationships of fluorinated carboxylic acid bioisosteres

Cited by 3 publications

References 10 publications

Hydroxytrifluoroethylation and Trifluoroacetylation Reactions via SET Processes

Hydroxytrifluoroethylation and Trifluoroacetylation Reactions via SET Processes

Bioisosterism in drug discovery

The Role of Small Molecules Containing Fluorine Atoms in Medicine and Imaging Applications

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