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Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity

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Author(s): Zrinka Rajic | Branka Zorc | Silvana Raic-Malic | Katja Ester | Marijeta Kralj | Krešimir Pavelic | Jan Balzarini | Erik De Clercq | Mladen Mintas

Journal: Molecules
ISSN 1420-3049

Volume: 11;
Issue: 11;
Start page: 837;
Date: 2006;
Original page

Keywords: Hydantoin | L- and D-amino acids | antiviral activity | antitumoral activity.

ABSTRACT
3,5-Disubstituted hydantoin (1,3-imidazolidinedione) derivatives 5a-h wereprepared by base induced cyclization of the corresponding N-(1-benzotriazolecarbonyl)-L-and D-amino acid amides 4a-h. Compounds 5a-h were evaluated for their cytostatic andantiviral activities. Among all the compounds evaluated, 3-benzhydryl-5-isopropylhydantoin (5a) showed a weak but selective inhibitory effect against vaccinia virus (EC50 =16 μg/mL; selectivity index: 25). 3-Cyclohexyl-5-phenyl hydantoin (5g) showed inhibitoryactivity against cervical carcinoma (HeLa, IC50 = 5.4 μM) and breast carcinoma (MCF-7,IC50 = 2 μM), but also cytotoxic effects towards human normal fibroblasts (WI 38). On thecontrary, the 3-benzhydryl-5-phenyl substituted hydantoin derivative 5h showed moderateinhibitory activity towards HeLa, MCF-7, pancreatic carcinoma (MiaPaCa-2), lungcarcinoma (H 460) and colon carcinoma (SW 620) (IC50 = 20−23 μM), but no effect on WI38.

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