Synthesis of azochalcone and azoflavone derivatives from chalcone (2E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one and study the antifungal activity for some of it

Abstract

Chalcone (2E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (A₁) was prepared in a new method by the condensation of ortho-hydroxyacetophenone with Para-dimethylaminobenzaldehyde using piperidine as an organic catalyst. A new series of azochalcone and azoflavone derivatives were synthesized from the                       chalcone (2E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl) prop-2-en-1-one by Diazotization - Coupling Reactions of different aromatic amines (o-aminophenol,        p-aminophenol, p-aminobenzoic acid) with chalcone. This is followed by the cyclization of azochalcone compounds using iodine and dimethyl sulfoxide DMSO. The physical and spectroscopic properties of the new compounds were studied (FT-IR,        ¹H-NMR, ¹³C-NMR). The purity of the synthesized compounds was confirmed using thin layer chromatography. The biological activity was studied on two synthetic flavonoids (B₅, B₆) at two different concentrations (0.5 mg/ml, 0.25 mg/ml) against three types of fungi: Aspergillus flavus, Acremonium strictum, Penicillium expansum. The compounds have showed good activity against the tested fungi.