Abstract
This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays. Keywords: oxazol-5(4H)-one, 1,2,4-triazin-6(5H)-one, cytotoxicity, Daphnia magna, Artemia salina
Highlights
Experimental partThe reactants and solvents used in the synthesis were purchased commercially with high purity and were used without further purification
This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes
We investigated the cytotoxicity of the new synthesized compounds using Daphnia magna and Artemia salina organisms
Summary
The reactants and solvents used in the synthesis were purchased commercially with high purity and were used without further purification. For the acquisition of the mass spectra of compounds a APCI (Atmospheric Pressure Chemical Ionization) mass spectrometer was used. A solution of about 0.5 mg /mL in chloroform was prepared and was diluted 10 times with methanol (1% formic acid) for positive ionization, when protonated molecular ions were obtained [M+H]+. For the synthesis of the new heterocycles from oxazolones and triazinones class we started to synthesize the 2-(4-(4-X-phenylsulfonyl) benzamido)acetic acids precursors using a multi-step reaction [37,38]. The condensation of the hippuric acids derivatives 4 with 4-iodobenzaldehyde, in the presence of acetic anhydride and sodium acetate, took place with the obtaining of the new benzylidene-oxazol-5(4H)-ones 5, namely 2-(4-(4-X-phenylsulfonyl)phenyl)-4-(4-iodobenzylidene)oxazol-5(4H)-ones. 3-(4-(4-X-phenylsulfonyl)phenyl)-5-(4-iodobenzylidene)-2-phenyl-1,2dihydro-1,2,4-triazin-6(5H)-ones 6a-c were obtained by treating of oxazolones 5a-c with phenylhydrazine, in the presence of acetic acid and sodium acetate. Cytoxicity evaluation The cytotoxicity bioassay was performed for compounds 5a-c, 6a,b and intermediates 4a-c.
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