One-pot four-component reactions of phenacyl bromides, parabanic or
thioparabanic acids, thiophenols, and triphenylphosphine in the presence of
triethylamine afforded new derivatives of hydantoin or thiohydantoin in
good to high yields (65%-90%). Their antibacterial activities were evaluated
against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Pseudomonas
aeruginosa). Among the synthesized compounds, the obtained products
from 2-hydroxythiophenol exhibited higher antibacterial activity than those
obtained from 2-aminothiophenol. Compound 9l including N,N0
0
-diphenyl
thiohydantoin moiety showed the highest antibacterial activity (26.0 ± 01.4)
against B subtilis, in comparison with other synthesized samples. The antioxidant activities of the synthesized hydant oins and thiohydantoins were investigated by DPPH radical-scavengi ng based on Blois method. The results showed
that all the compounds have high DPPH inhibition potency (77.4%-83.9%) that
it could be due to existence of heteroatoms with lone pair electrons and
exchangeable protons on their NH2 and OH groups.