Synthèse, Séparation Chirale Et Evaluation Biologique Des Dérivés 4-iminoflavan

Résumé: This work was interested in the synthesis, biological activity and chiral separation of enantiomers and diastereomers of 4-Iminoflavane derivatives. First we synthesized a new molecules from flavanone by a simple and easy methods. These syntheses are based on condensation and reduction reactions using as reagents primary amines and pyridine. This allowed us to prepare twenty-one new Flavanone derivatives, which not described until today. The structures of these compounds have been proved by spectroscopic methods IR, UV, RMN1H and RMN13C. The HPLC enantiomeric separation of all products 2-22 was accomplished in the normal phase and organic polar mode, using six polysaccharides derived chiral stationary phases (Chiralcel®OD-H, Chiralcel®OD, Chiralcel®OJ, Chiralpak®AD, Chiralpak®IA and Chiralpak®IB) and various nalkane/alcohol mobile phases. The enantioseparation of these new prepared shows that the chiral recognition mechanism of each stationary phase has been suggested, and based on the chemical nature and conformation of the chiral selector. Finally, all the synthesis products undergone varied biological activities (antioxidants, antibacterials and antifungals). For our tests against bacteria, the results were different and mostly positive for all compounds. The antifungal tests against Fusarium oxysporum f.sp. albedinis were negative. Used for the antioxidant test, the following three techniques : scavenging of the radical DPPH, ferric reducing-antioxidant power (FRAP) and the β- carotene tested. The results of antioxidant activity showed that most derivatives have a high inhibitory ability against radicals in particular the 4- imnoflavans.

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