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Molecules 2006, 11(11), 837-848; doi:10.3390/11110837
Article

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

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Received: 6 October 2006; in revised form: 25 October 2006 / Accepted: 25 October 2006 / Published: 1 November 2006
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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.
Keywords: Hydantoin; L- and D-amino acids; antiviral activity; antitumoral activity. Hydantoin; L- and D-amino acids; antiviral activity; antitumoral activity.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Rajic, Z.; Zorc, B.; Raic-Malic, S.; Ester, K.; Kralj, M.; Pavelic, K.; Balzarini, J.; De Clercq, E.; Mintas, M. Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity. Molecules 2006, 11, 837-848.

AMA Style

Rajic Z, Zorc B, Raic-Malic S, Ester K, Kralj M, Pavelic K, Balzarini J, De Clercq E, Mintas M. Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity. Molecules. 2006; 11(11):837-848.

Chicago/Turabian Style

Rajic, Zrinka; Zorc, Branka; Raic-Malic, Silvana; Ester, Katja; Kralj, Marijeta; Pavelic, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen. 2006. "Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity." Molecules 11, no. 11: 837-848.



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