Synthesis and evaluation of biological activity of imidazolidinone analogues of 2-aminochromone

The chromone heterocycle is a potential pharmacophore that is present in flavonoids. These flavonoids possess a variety of biological activities including the anticancer activity. Imidazolidinones are another group of heterocycles known for its wide range of pharmacological activities. In this work, the imidazolidinone ring was incorporated onto the chromone structure in an attempt to obtain a synergistic activity of both the ring systems. Synthesis was achieved by condensing 2-aminochromone with azlactones. The synthesis of aminochromone and its imidazolidinone analogues were confirmed by the mass spectral analysis followed by the 1H NMR, UV and IR spectral analysis. The newly synthesized imidazolidinone analogues were screened for their cytotoxic, antioxidant, and anti-inflammatory activity. The in vitro cytotoxic screen was performed on human cancer cell lines by the Microculture Tetrazolium (MTT) assay. The cell lines used were HeLa (Epithelial human cervix cancer cell line) and MDA MB 435 (Human breast cancer cell line). Antioxidant screening was carried out using colorimetric assays. The anti-inflammatory potential was evaluated by an in vivo Carrageenan induced rat paw edema model. The results obtained for cytotoxicity study showed that, the imidazolidinone derivatives enhanced the cytotoxic potential of the 2-aminochromones by five times with the highly potent derivative showing anIC50 of 19.78 μg/ml. The results obtained for the antioxidant and anti-inflammatory studies are also in conformity with the results of cytotoxic screen where in the analogues registering an enhanced activity in comparison to the aminochromone.