Synthèse de Chalcones adamantylées, de dérivés Thiazolylpyrazolines et évaluation de leurs activités antimicrobienne et anticancéreuse

Abstract

The main objective of this work is the synthesis and the biological evaluation of original compounds with medicinal potential. In the first part, a new variety of adamantyl chalcones was efficiently prepared by ClaisenSchmidt reaction of 4-adamantyl acetophenone with a series of aromatic aldehydes in good yields. Their structures were confirmed by spectroscopic data, and the relative configuration of compound 3d was confirmed by X-ray crystallography. All synthesized chalcones were tested against a panel of Gram-positive and Gram-negative bacteria and pathogenic fungus. They displayed a strong antibacterial activity against Enterococcus faecali 29212, Pseudomonas aeruginosa ATCC27853, Escherichia coli, as well as an interesting antifungal activity against Candida glabrata ATCC 90030. The effect of these compounds was also tested in vitro as antitumor on Miapaca2 cells. The compounds also showed anticancer activity against human pancreas cancer cell MiaPaca2. In the second part, several thiazolyl-pyrazoline derivatives were synthesized by reacting substituted 3, 5-diaryl-1-thiocarbamoyl-2-pyrazolines with phenacylbromides. The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, and MS spectral data. Their antimicrobial, anticancer activities and cytotoxicity were investigated. A significant level of antimicrobial activity and anticancer activity against A549 human lung carcinoma cell line and low cytotoxicity were observed.