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, (1)H-NMR and (13)C-NMR spectroscopy, and by using a combination of 2D NMR experiments, which included (1)H-(1)H 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 (1)H and (13)C 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.
Highlights
Hydantoins, or 2,4-imidazolidinediones are compounds of considerable interest both from a chemical and biological point of view.[1]
Kato et al investigated the effects of novel aldose reductase inhibitors, M16209 (1-(3-bromobenzo[b]furan-2-ylsulfonyl)hydantoin) and M16287 (1-(3-chlorobenzo[b]furan-2-ylsulfonyl)hydantoin), on neuropathy in streptozotocin-induced (STZ) diabetic rats.[19]
The goal of the present paper is to describe a method for synthesis of 3-methyl-9’-fluorenespiro-5-hydantoin, its structural elucidation and biological properties
Summary
Hydantoins, or 2,4-imidazolidinediones are compounds of considerable interest both from a chemical and biological point of view.[1]. Palm et al investigated the influence of diabetes-induced changes in oxygen tension and consumption in relation to regional renal metabolism in rats.[17] In the second set of experiments, the putative role of the polyol pathway for hyperglycaemiainduced alterations in renal metabolism was studied. Two potent aldose reductase inhibitors, l-[(2,5dichlorophenyl)sulfonyl]hydantoin (Di-ClPSH) and 1[β-naphthyl)sulfonyl]hydantoin (β-NSH), were tested for usefulness in the treatment of diabetic and galactosemic complications in animal experiments.[22]
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