Browsing by Author "Mardanov, Aladdin"
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- Mechanosynthesis of bioactive compounds based on natural scaffoldsPublication . Mardanov, Aladdin; Bonifácio, Vasco D.B.; Cavaco , Isabel M.P.A.This thesis explored the use of mechanochemistry as a green methodology to prepare bioactive molecules. The synthetic methodology searched the preparation of different classes of compounds, using organic reactions comprising acylation and substitution reactions. The main focus of the work was the development of a robust methodology that could lead to the preparation of bioactive compounds, based on natural scaffolds, optimizing the existing protocol by removing solvents, reducing reaction time, and energy. For this purpose work considers manufacturing of compounds and the formation of their intermediates using mechanochemistry. Nevertheless, the main area of focus is testing of this reactions and synthetic pathways to form new APIs based on natural compounds or optimize existing reactions by removing solvent use, reducing reaction time, and energy use, since the aim is to make processes follow green chemistry and sustainable manufacturing practices. In other words, the idea beyond the manufacturing is to use compounds found in nature (extracted from vegetation). Coumarins were selected as key scaffolds due to their interesting properties, showing evidence of biological activity, especially their derivatives. In this work, coumarins were first synthesized and then acylated to produce derivatives compounds with enhanced bioactivity. The synthesis of coumarins from salicylaldehydes was attempted by mechanosynthesis but discarded due to lower yields, attributed to the lower temperatures reached under ball milling conditions. This reaction step was investigated using ultrasound irradiation, which proved to be successful, and showed to be an alternative methodology to the conventional approach using water under refluxing conditions. Coumarins acylation was performed using mechanochemistry, with good yields, under solventless conditions, no external heating, and reduced reactions times. This methodology allowed the synthesis of two new coumarins (biscoumarins) and four new coumarin derivatives. The mechanosynthesis of flavonoid derivatives was also investigated, with good results. Finally, the mechanosynthesis of benzoin derivatives was explored, but in this case the target compounds were not observed.