Synthesis, characterization and Cytotoxicity Evaluation of New Heterocyclic Compounds with Oxazole Ring Containing 4-(Phenylsulfonyl)phenyl Moiety

doi:10.37358/10.37358/rc.70.19.11.7649

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. Keywords: N-acyl-a-amino acid, 1,3-oxazol-5(4H)-one, N-acyl-a-amino ketone, 1,3-oxazole, cytotoxic effect

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

Introduction

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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