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.