The Synthesis and Biological Activities Of Some New 2-(4-Methoxy-phenoxymethyl)benzoic Acid Thioureides

The Synthesis and Biological Activities Of Some New 2-(4-Methoxy-phenoxymethyl)benzoic Acid Thioureides

Abstract:

This paper presents the synthesis, structure confirmation and biological (antimicrobial and cytotoxicity) activities of some new 2-(4-methoxy-fenoxymethyl)benzoic acid thioureides. The new thioureides were obtained in three stages. In the first stage we prepared the 2-(4-methoxy-fenoxymethyl)benzoic acid by reacting potassium para-methoxy-phenoxide with phtalide. The second stage consisted in the synthesis of the 2-(4-methoxy-fenoxymethyl) benzoic acid chloride and in the third phase, the acid chloride afore mentioned was refluxed with ammonium thiocyanate and the resulting 2-(4-methoxy-fenoxymethyl)benzoyl isothiocyanate was treated with primary aromatic amines to obtain the new compunds. The new synthetised compounds structures were confirmed by spectral 1H-NMR, 13C-NMR and elemental analysis. The in vitro antimicrobial activity was evaluated using qualitative screening of the susceptibility spectra of different microbial strains to these compounds by three adaptated diffusion methods: paper filter disk impregnation with the tested substances solutions, the disposal of tested solutions in agar wells and the spotting of tested solutions on microbial inoculums seeded medium. The quantitative assay of the antimicrobial activity was performed by nutrient broth microdilution method in order to establish the minimal inhibitory concentration (MIC). The new thioureides presented a significant antimicrobial activity with MICs ranging from 128 mg/ mL to 256 mg/mL. The tested compounds exhibited reduced cytotoxicity on different cell lines and influenced the eukariotic cell cycle. Key words: thioureides, antimicrobial activity, cytotoxicity

Issue: 2007, Volume 58, Issue 11

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This article is published under the Creative Commons Attribution 4.0 International License

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