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Phenyl isothiocyanate: Synthesis and biological potential

The sulfur-containing compounds, glucosinolates, a class of secondary metabolites are found in almost all plants of the order Capparales, in particular in the family Brassicaceae (e.g. broccoli and other cabbages). Glucotropaeolin, a glucosinolate associated with an uncommon endogenous glucohydrolase-myrosinase (E.C.3.2.1.147), operates like precursor to phenyl isothiocyanate. In order to investigate its biological properties the pure phenyl isothiocyanate was obtained by one-pot synthesis by reaction of aniline with CS2 in aqueous K2CO3 solutions affording the dithiocarbamate intermediate, which was further desulfurized with cyanuric acid at 0 °C to provide the corresponding phenyl isothiocyanate. The obtained compound was confirmed by GC-MS and spectroscopic techniques (FTIR, 1D and 2D NMR). Phenyl isothiocyanate was tested for its antioxidative (using FRAP, DPPH and Briggs-Rauscher methods), anticancer (using MTT method), and cholinesterase inhibitory activities (using Ellman method). These investigations confirmed this secondary metabolite to be a compound of primary interest.

Phenyl isothiocyanate; Synthesis; Antioxidant activity; Anticancer activity; Cholinesterase inhibition; NMR

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