Synthesis and evaluation of biological activities of tripodal imines and β-lactams attached to the 1,3,5-triazine nucleus

A novel collection of tripodal β-lactam derivatives with 1,3,5-triazine as the central core is presented for the first time. The diastereoselective synthesis of tris-β-lactams was achieved via a [2 + 2] cycloaddition reaction between s-triazine-based tris-imines and activated aryloxyacetic acid derivatives. All the s-triazine hybrids were identified by FT-IR, ¹H NMR, ¹³C NMR spectroscopies and elemental analysis, and found to have all-cis relative stereochemistry of the three β-lactams rings. The intermediate imines displayed moderate in vitro inhibitory activity against MCF-7 and HeLa cancer cell lines. The tris-β-lactams were tested against four kinds of bacteria including Gram-negative bacteria, E. coli and P. aeruginosa, a Gram-positive S. aureus and one capsulated Gram-negative K. pneumonia by the Kirby–Bauer disc diffusion method. Two compounds have shown moderate antibacterial activity against S. aureus, but not against the other bacteria, or fungal isolates C. albicans and A. fumigatus. The tris-β-lactams displayed good inhibitory behavior against the K562 human leukemia cell line, and antioxidant properties as radical scavengers. Graphic abstract: