Enaminoketones - functional derivatives based on 7-hydroxy-3′,3′-dimethyl-3′<i>H</i>-spiro[chromen-2,1′-isobenzofuran]-8-carbaldehyde with aromatic amines. physicochemical studies and biological activity

Abstract

This research focuses on studying derivatives of 2-oxaindane spiropyran by its condensation with aromatic amines. The results showed that all the synthesized compounds are enaminoketones form in both solution and solid state. This is explained by the fact that during the formation of Schiff bases, the proton of the 7-hydroxyl group of the benzopyran part migrates to the azomethine nitrogen, which leads to the transition of the cyclic form of spiropyran into the corresponding enaminoketone. In the DMSO solution, the enaminoketones dynamic equilibrium of the E , Z -isomeric forms were observed. The structure of enaminoketone based on 3,4-dimethylaniline was proved by the X-ray diffraction method. The synthesized compounds were studied for their in vitro anticancer activity against human hepatocellular carcinoma (HepG2), breast carcinoma (MCF-7), lung cancer (A549), and carcinoma cells (KB). Enaminoketone with R = 3,4-СH3Ph is characterized by the highest activity, with IC50 values of 13.38 μM (KB). The results in vitro antioxidant activity test using 1,1-diphenyl-2-picrylhydrazyl (DPPH) indicated that enaminoketones were inactive.