57128-29-7Relevant academic research and scientific papers
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.
Stereoinversion in the diastereoselective acylation of benzoxazine derivatives with 2-aryloxypropionyl chlorides
Vakarov,Korolyova,Gruzdev,Pervova,Levit,Krasnov
, p. 1257 - 1263 (2019/07/15)
A comparative study of the kinetic resolution of racemic derivatives of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine using racemic 2-aryloxypropionyl chlorides was performed. It was found that the acylation of racemic amines with racemic 2-(1-naphthyloxy)propionyl chloride leads to amides enriched with (3R*,2′R*)-diastereomers, while the acylation with 2-phenoxypropionyl chloride gives predominantly (3R*,2′S*)-amides. Quantum chemical modeling of the process of kinetic resolution at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP//B3LYP-D3-gCP/def2-SVP level of theory was performed. The computational results are in a good agreement with the experimental data.
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.
A new method for production of chiral 2-aryloxypropanoic acids using effective kinetic resolution of racemic 2-aryloxycarboxylic acids
Tengeiji, Atsushi,Nakata, Kenya,Ono, Keisuke,Shiina, Isamu
, p. 1227 - 1252 (2013/08/23)
We report a novel method for the preparation of 2-aryloxypropanoic acids by kinetic resolution of racemic 2-aryloxypropanoic acids using enantioselective esterification. The usage of pivalic anhydride (Piv2O) as an activating agent, bis(a-naphthyl)methanol ((α-Np)2CHOH) as an achiral alcohol, and (+)-benzotetramisole ((+)-BTM) as a chiral acyl-transfer catalyst enables the effective separation of various racemic 2-aryloxypropanoic acids to afford optically active carboxylic acids and the corresponding esters with high enantioselectivities. Furthermore, theoretical calculations of the transition states required to form the chiral esters successfully proved the enantiomer recognition mechanism of the asymmetric esterification.
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.
Enantioselective Hydrolysis of Aryloxypropionic Esters by Bovine Serum Albumin: Enhancement in Selectivity by β-Cyclodextrin
Kamal, Ahmed,Ramalingam, T.,Venugopal, N.
, p. 39 - 42 (2007/10/02)
Bovine serum albumin catalyzed hydrolysis of racemic aryloxypropionic esters affords appreciable enantioselectivity.The effect of β-cyclodextrin this process of hydrolysis has been studied.
