A review: FDA-approved fluorine-containing small molecules from 2015 to 2022

Sheikhi, Negar; Bahraminejad, Maryam; Saeedi, Mina; Mirfazli, Seyedeh Sara

doi:10.1016/j.ejmech.2023.115758

Cited by 23 publications

(2 citation statements)

References 182 publications

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“…Fluoroquinolone antibiotics (FQs) are a class of synthetic antimicrobial agents with a fluorine atom present within their chemical structure, typically attached to a quinolone ring. They possess potent antibacterial activity and have been widely used in clinical medicine to combat a broad spectrum of bacterial infections 1 . FQs are appreciated for their broad spectrum of action.…”

Section: Introductionmentioning

confidence: 99%

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Rudnicki,

Budzyńska,

Skrzypek

et al. 2024

Sci Rep

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This work compares the electroanalytical performance of two electroanalytical systems based on (1) the glassy carbon electrode (GCE), and (2) the electrified liquid–liquid interface (eLLI), for the detection of fluoroquinolone antibiotic–danofloxacin (DANO). Our aim was to define the optimal conditions to detect the chosen analyte with two employed systems, extract a number of electroanalytical parameters, study the mechanism of the charge transfer reactions (oxidation at GCE and ion transfer across the eLLI), and to provide physicochemical constants for DANO. Detection of the chosen analyte was also performed in the spiked milk samples. To the best of our knowledge, this is the first work that directly compares the electroanalytical parameters obtained with solid electrode (in this case GCE) and eLLI. We have found that for DANO the latter provides better electroanalytical parameters (lower LOD and LOQ) as well as good selectivity when the milk was analyzed.

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Section: Introductionmentioning

confidence: 99%

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Rudnicki,

Budzyńska,

Skrzypek

et al. 2024

Sci Rep

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“…The introduction of fluorine into organic molecules is of utmost importance in the preparation of active pharmaceutical ingredients (APIs). − Since 2016, up to 44% of FDA-approved small-molecule APIs per year contained at least one fluorine atom. − It is estimated that a drug containing a fluorine atom is 10 times more likely to be successful, as fluorine provides an improved metabolic stability, better physiochemical properties, and enhanced binding interactions. , Fluorine is also used in positron emission tomography (PET) as a radiopharmaceutical due to the relatively long half-life of the 18 F isotope . In particular, the CF 2 moiety is a very special motif in biologically active molecules, as the beneficial effects mentioned earlier are potentially doubled with the presence of two fluorine atoms on the same carbon.…”

Section: Introductionmentioning

confidence: 99%

Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF₄) and Dialkylamines in Continuous Flow Mode

Polterauer,

Wagschal,

Bersier

et al. 2024

Org. Process Res. Dev.

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Fluorinated molecules are prevalent in biologically active substances, in particular, the gem-difluoro motif. However, the selective incorporation of a gem-difluoro motif into organic molecules is a laborious task. Deoxyfluorination is a promising and widely used methodology to achieve this transformation, which is usually costly or highly hazardous. Herein, we report a deoxyfluorination protocol using sulfur tetrafluoride (SF 4 ) and diethylamine (Et 2 NH) to prepare gem-difluorides in continuous flow mode. The process does not require the addition of exogenous HF, and in situ generated reagents were quenched in-line, which improved safety. The methodology was successfully applied to convert a broad range of 4-, 5-, and 6-membered ketone derivatives to their corresponding difluorinated compounds while minimizing the undesired vinyl fluoride formation. In summary, these findings improve safety and selectivity toward the synthesis of gem-difluoro compounds drastically, enabling a more efficient production of fluorinated active pharmaceutical ingredients.

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Ruthenium(II)‐Catalyzed Enantioselective Synthesis of 1,2‐trans‐Disubstituted PhSO₂CF₂‐containing Cyclopropanes

Zhao,

Besset,

Jubault

2024

Adv Synth Catal

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The direct diastereo‐ and enantioselective Ru(II)‐ catalyzed cyclopropanation reaction of alkenes with ((2‐diazo‐1,1‐difluoroethyl)sulfinyl)benzene was described. The desired enantioenriched PhSO2CF2‐cyclopropanes were obtained in high yields with high diastereo‐ and enantioselectivities in the presence of a chiral ruthenium complex Ru(II)‐Pheox (17‐94% yields, >20:1 d.r. and 83:17‐98:2 e.r.). The robustness of the approach was showcased and This methodology gave access to chiral 1,2‐trans difluoro‐methylcyclopropanes.

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A review: FDA-approved fluorine-containing small molecules from 2015 to 2022

Cited by 23 publications

References 182 publications

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF₄) and Dialkylamines in Continuous Flow Mode

Ruthenium(II)‐Catalyzed Enantioselective Synthesis of 1,2‐trans‐Disubstituted PhSO₂CF₂‐containing Cyclopropanes

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A review: FDA-approved fluorine-containing small molecules from 2015 to 2022

Cited by 23 publications

References 182 publications

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Comparative electrochemical study of veterinary drug danofloxacin at glassy carbon electrode and electrified liquid–liquid interface

Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF4) and Dialkylamines in Continuous Flow Mode

Ruthenium(II)‐Catalyzed Enantioselective Synthesis of 1,2‐trans‐Disubstituted PhSO2CF2‐containing Cyclopropanes

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Product

Resources

About

Deoxyfluorination of Ketones with Sulfur Tetrafluoride (SF₄) and Dialkylamines in Continuous Flow Mode

Ruthenium(II)‐Catalyzed Enantioselective Synthesis of 1,2‐trans‐Disubstituted PhSO₂CF₂‐containing Cyclopropanes