57128-29-7Relevant articles and documents
HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
, p. 900 - 907 (2021/06/07)
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
Synthesis of Naphthyl-, Quinolin- and Anthracenyl Analogues of Clofibric Acid as PPARα Agonists
Giampietro, Letizia,Ammazzalorso, Alessandra,Bruno, Isabella,Carradori, Simone,De Filippis, Barbara,Fantacuzzi, Marialuigia,Giancristofaro, Antonella,Maccallini, Cristina,Amoroso, Rosa
, p. 467 - 471 (2016/03/12)
PPARα is a ligand activated transcription factor belonging to the nuclear receptor subfamily, involved in fatty acid metabolism in tissues with high oxidative rates such as muscle, heart and liver. PPARα activation is important in steatosis, inflammation and fibrosis in preclinical models of non-alcoholic fatty liver disease identifying a new potential therapeutic area. In this work, three series of clofibric acid analogues conjugated with naphthyl, quinolin, chloroquinolin and anthracenyl scaffolds were synthesized. In an effort to obtain new compounds active as PPARα agonists, these molecules were evaluated for PPARα transactivation activity. Naphthyl and quinolin derivatives showed a good activation of PPARα; noteworthy, optically active naphthyl derivatives activated PPARα better than corresponding parent compound.
Synthesis of 2-aryloxypropanoic acids analogues of clofibric acid and assignment of the absolute configuration by 1H NMR spectroscopy and DFT calculations
Ammazzalorso, Alessandra,Bettoni, Giancarlo,De Filippis, Barbara,Fantacuzzi, Marialuigia,Giampietro, Letizia,Giancristofaro, Antonella,Maccallini, Cristina,Re, Nazzareno,Amoroso, Rosa,Coletti, Cecilia
, p. 989 - 997 (2008/09/21)
A new set of optically active 2-aryloxypropanoic acids has been synthesized through a simple strategy, in good yields and excellent enantiomeric excesses. Their absolute configuration was assigned by means of a NMR-based approach consisting of the derivatization of the carboxylic acids with ethyl mandelate and the comparison of the chemical shifts of the obtained diastereomers. The effectiveness of such an approach has been tested against a larger set of chiral α-substituted-carboxylic acids and by performing high level density functional theory (DFT) calculations on a set of low energy conformations for each diastereomeric derivative. The employed computational procedure has enabled us to find a semiquantitative relationship between the experimental NMR data and the theoretically calculated energy gaps which confirms the theoretical foundations of the NMR strategy and allows to understand when and why it is most likely to fail.
