Synthesis, characterisation and biological evaluation of fluorinated chalcones.

Abstract

Chalcones, also known as a-,b-unsaturated ketones, have demonstrated various biological functions. The production of chalcone and fluoro-substituted derivatives (1-11) (Fig. 1) was carried out by Claisen-Schmidt condensation reaction in an alkali medium (Scheme 1). The 1 H nuclear magnetic resonance (NMR), the 13C NMR, the 19F NMR, the infrared (IR), and the mass spectroscopy (MS) were used to characterise all the products. The yield of the chalcone compounds was reported in moderate to high percentages. Chalcone 11 was transformed to indole 12 in a low yield. Compounds 1, 4, 7 and 10 were tested against bacteria and fungi to evaluate their antimicrobial activity. Compounds 1 and 4 showed promising results in fungi plates, which appeared as growth reduction. More analogues could be obtained by the Claisen-Schmidt condensation reaction due to its ease of synthesis