One-pot synthesis of novel (2R,4S)-N-aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl) pyrrolidine-2-carboxamides via TiO2-NPs and Pd(PPh3)2Cl2 catalysts and investigation of their biological activities

A new class of (2R,4S)- N -aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide compounds was synthesized by a facile one-pot reaction of trans-4-hydroxy proline and trifluoroacetimidoyl chlorides in the presence of TiO 2 -nanoparticles as a catalyst and sodium bicarbonate as a base. Sy...

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Veröffentlicht in:Molecular diversity 2017-05, Vol.21 (2), p.305-315
Hauptverfasser: Darehkordi, Ali, Ramezani, Mahin
Format: Artikel
Sprache:eng
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Zusammenfassung:A new class of (2R,4S)- N -aryl-4-hydroxy-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide compounds was synthesized by a facile one-pot reaction of trans-4-hydroxy proline and trifluoroacetimidoyl chlorides in the presence of TiO 2 -nanoparticles as a catalyst and sodium bicarbonate as a base. Synthesized compounds showed cytotoxicity with IC 50 values of 15.3–70.3  μ M against K562 (Homo sapiens, human) cells. The results of the study provide a valuable method for one-pot synthesis of trans-4-hydroxy proline-based N -(2,2,2-trifluoroacetylated) compounds. Also, these compounds show significant pharmaceutical activities as antibacterial and antifungal reagents. Graphical Abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-017-9726-y