Synthesis and structure elucidation of aminoalkoxy-substituted chalcones with potential biological activity

The research for this experimental thesis in Pharmaceutical Chemistry and Technology was carried out at the Faculty of Pharmacy of the University of Porto (Portugal), in the Laboratory of Organic and Pharmaceutical chemistry under supervision of Prof. Honorina Cidade, as part of the Erasmus+ international mobility programme. The objective of this research is the synthesis of pharmaceutical compounds intended for use in subsequent experimental phases aimed at evaluating their biological activities. Five aminoalkoxychalcones were synthesized starting from 2,4-dihydroxyacetophenone, using 5 different aliphatic amines. The synthesis consists of two parts. The first reaction is a SN2 between the hydroxy acetophenone and a β-ammino haloalkane. The second reaction involves the amminoacetophenone obtained from the previous reaction and 3,4,5-trimethoxybenzaldehyde. The reactions were monitored and analysed by thin-layer chromatography. The obtained products were purified using column chromatography, solvent extraction, preparative-thin layer chromatography and crystallization. They were then analysed through NMR and HRMS. The preparation of these derivatives represents a strategic step toward the development of novel therapeutic agents, as it offers the potential to obtain molecules exhibiting a range of biological properties, including antitumor, anti-inflammatory, antioxidant, and antibiotic activities.