62806-35-3Relevant academic research and scientific papers
2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids are novel substrates of phenylalanine ammonia-lyase
Paizs, Csaba,Tosa, Monica Ioana,Bencze, Laszlo Csaba,Brem, Juergen,Irimie, Florin Dan,Retey, Janos
, p. 1217 - 1228 (2011/05/05)
Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, 1H-NMR and 13C-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-la) para-Br (rac-lb) or Cl para or ortho (rac-lc, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10. The Japan Institute of Heterocyclic Chemistry.
Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
Wiesner, Jochen,Mitsch, Andreas,Wissner, Pia,Kraemer, Oliver,Jomaa, Hassan,Schlitzer, Martin
, p. 2681 - 2683 (2007/10/03)
In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties.
ARYLATION OF FURAN COMPOUNDS BY ARENEDIAZONIUM SALTS
Obushak, N. D.,Ganushchak, N. I.,Lesyuk, A. I.,Dzikovskaya, L. M.,Kisilitsa, P. P.
, p. 748 - 753 (2007/10/02)
3-(5-Aryl-2-furyl)acrylic acids were obtained by the reaction of 5-arylfurfurals with malonic acid.They were arylated by diazonium salts with decarboxylation and the formation of 5-aryl-2-styrylfurans.The latter were also obtained by the interaction of furylacrolein with diazonium salts.This reaction also gave 3-(5-aryl-2-furyl)acroleins and the corresponding arylfurylacrylic acids, which were arylated again with the release of CO2 and the formation of 5-aryl-2-styrylfurans. 3-(5-Aryl-2-furyl)acroleins were also synthesized by the condensation of 5-arylfurfurals with acetaldehyde under phase-transfer conditions.The s-trans configuration of the furan ring and the exocyclic double bond were established in the obtained compounds by the PMR method.
