Abstract
The paper presents the synthesis, characterization and cytotoxicity assessment of five organic compounds containing 4-(phenylsulfonyl)phenyl fragment in the molecule, namely of three acyclic precursors derived from phenylalanine (from N-acyl-a-amino acids, N-acyl-a-amino acyl chlorides and N-acyl-a-amino ketones class) and of the cyclization products: a 1,3-oxazol-5(4H)-one and, respectively, a 1,3-oxazole substituted in position 5 with the p-tolyl group. The synthesized compounds were characterized by spectral methods (UV-Vis, FT-IR, 1H-NMR, 13C-NMR, and MS) and elemental analysis, which confirmed their structures. For the determination of the purity of the new compounds, the RP-HPLC method was used. In view of the therapeutic potential of the newly synthesized compounds, we evaluated their toxicological profile using the Daphnia magna bioassay.
Highlights
The paper presents the synthesis, characterization and cytotoxicity assessment of five organic compounds containing 4-(phenylsulfonyl)phenyl fragment in the molecule, namely of three acyclic precursors derived from phenylalanine and of the cyclization products: a 1,3-oxazol-5(4H)-one and, respectively, a 1,3-oxazole substituted in position 5 with the p-tolyl group
Open-chain intermediates from N-acyl-α-amino acid and N-acyl-α-amino ketone classes are known in the literature as active substances with significant biological properties
Five new compounds from N-acyl-α-amino acid, N-acylα-amino acid chloride, 1,3-oxazol-5(4H)-one, N-acyl-áamino ketone, and 1,3-oxazole class, which contain in the structure a 4-(phenylsulfonyl)phenyl moiety, were synthesized and characterized
Summary
The paper presents the synthesis, characterization and cytotoxicity assessment of five organic compounds containing 4-(phenylsulfonyl)phenyl fragment in the molecule, namely of three acyclic precursors derived from phenylalanine (from N-acyl-α-amino acids, N-acyl-α-amino acyl chlorides and N-acyl-α-amino ketones class) and of the cyclization products: a 1,3-oxazol-5(4H)-one and, respectively, a 1,3-oxazole substituted in position 5 with the p-tolyl group. With the exception of N-acyl-α-amino acyl chlorides - which are known to have a high reactivity - these compounds have attracted the attention due to importance in the field of medicinal chemistry because of their diverse biological activities In this regard, the 1,3-oxazole ring is found in the structure of various biologically active natural products, such as Martefragin A (a potent inhibitor of lipid peroxidation). The 5-hydroxy-substituted 1,3-oxazoles derived from N-acyl-α-amino acids (the aromatic enol form) exist in their corresponding nonaromatic oxo form: the saturated 1,3-oxazol-5(4H)-ones, classically referred to as saturated azlactones Some representatives of this class have been reported to possess antiviral [13], antitumoral [14], cytotoxic [15], plant growth regulating activity [16].
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