Abstract

3-Fluorothalidomide, a nonracemizable isosteric analogue of thalidomide, was successfully prepared by perchloryl fluoride fluorination of a 3-phthalimidopiperidin-2-one derivative followed by RuO2 oxidation. In the preliminary biological evaluation of (R)- and (S)-enantiomers, it was shown that the (S)-isomer was found to be more active than both the (R)-isomer and the racemic thalidomide in lipopolysaccharide-induced TNF-α production enhancement produced from human peripheral blood lymphocytes cultivated in vitro.

Keywords

ThalidomideChemistryEnantiomerStereochemistryIn vitroDerivative (finance)LipopolysaccharideBiochemistryImmunology

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Publication Info

Year
1999
Type
article
Volume
1
Issue
10
Pages
1571-1573
Citations
96
Access
Closed

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Yoshio Takéuchi, Tomoki Shiragami, Kenichi Kimura et al. (1999). (<i>R</i>)- and (<i>S</i>)-3-Fluorothalidomides:  Isosteric Analogues of Thalidomide. Organic Letters , 1 (10) , 1571-1573. https://doi.org/10.1021/ol9902172

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DOI
10.1021/ol9902172