Synthesis, characterization and cytotoxicity assessment of new 4-benzyl-1,3-oxazole derivatives incorporating 4-[(4-bromophenyl)sulfonyl]phenyl fragment

Abstract

Herein we present the design, synthesis, characterization, and cytotoxicity assessment of seven compounds derived from phenylalanine that incorporate a 4-[(4-bromophenyl)sulfonyl]phenyl fragment: four open-chain products (one N-acyl-α-amino acid, one N-acyl-α-amino acyl chloride, two N-acyl-α-amino ketones), and three five-membered heterocycles with two heteroatoms (O and N): one 2-aryl-4-benzyl-1,3-oxazol-5(4H)-one, and two 2-aryl-4-benzyl-1,3-oxazoles with p-tolyl, and m-xylyl substituent, respectively, in position 5. Structures of new derivatives were assigned by elemental analysis, NMR spectroscopy, and other spectral methods (FT-IR, MS, UV-Vis). Evaluation of the purity of the compounds was realized by reversed-phase high-performance liquid chromatography. Daphnia magna toxicological test was used to assess the cytotoxicity of new compounds.