Study on the synthesis, characterization and bioactivities of 3-methyl-9′-fluorenespiro-5-hydantoin

Abstract

This work describes a method for synthesis, as well as in vitro antiproliferative and antibacterial investigation of 3-methyl-9′-fluorenespiro-5-hydantoin. The structure of the substituted fluorenylspirohydantoin derivative was verified by UV-Vis, FT-IR, Raman, 1H-NMR and 13C-NMR spectroscopy, and by using a combination of 2D NMR experiments, which included 1H-1H COSY, HMQC and HMBC sequences. The geometry of the compound was optimized by the B3LYP density functional with 6-31G(d) basis set and the 1H and 13C NMR spectra were predicted with the HF/6-31G(d) calculations at the optimized geometry. The anticancer activity of the 3-methyl-9′-fluorenespiro-5-hydantoin was determined in suspension cell lines originating from tumors in humans (WERI-Rb-1). The cytotoxic effect was evaluated by WST-assay (Roche Applied Science). The antimicrobial effect of the compound against Gram-negative, Gram-positive bacteria and the yeast Candida albicans was investigated.

Keywords

• 3-methyl-9′-fluorenespiro-5-hydantoin
• NMR spectra
• cytotoxic activity
• antimicrobial effect