Romanian Society of Pharmaceutical Sciences
 

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SYNTHESIS, CHARACTERIZATION AND CYTOTOXICITY ASSESSMENT OF NEW 4-BENZYL-1,3-OXAZOLE DERIVATIVES INCORPORATING 4-[(4-BROMOPHENYL)SULFONYL]PHENYL FRAGMENT

THEODORA VENERA APOSTOL 1*, CONSTANTIN DRĂGHICI 2, LAURA ILEANA SOCEA 1,
OCTAVIAN TUDOREL OLARU 3, GABRIEL ȘARAMET 4, MĂDĂLINA HRUBARU 2,
ȘTEFANIA FELICIA BĂRBUCEANU 1

1“Carol Davila” University of Medicine and Pharmacy, Faculty of Pharmacy, Organic Chemistry Department, 6 Traian Vuia Street, 020956, Bucharest, Romania
2“Costin D. Nenițescu” Institute of Organic Chemistry, Romanian Academy, 202B Splaiul Independenței Street, 060023, Bucharest, Romania
3“Carol Davila” University of Medicine and Pharmacy, Faculty of Pharmacy, Pharmaceutical Botany and Cell Biology Department, 6 Traian Vuia Street, 020956, Bucharest, Romania
4“Carol Davila” University of Medicine and Pharmacy, Faculty of Pharmacy, Pharmaceutical Technology and
Biopharmacy Department, 6 Traian Vuia Street, 020956, Bucharest, Romania

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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 highperformance liquid chromatography. Daphnia magna toxicological test was used to assess the cytotoxicity of new compounds.