Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity
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 evaluate...
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MDPI AG
2006-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/11/11/837/ |
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doaj-a9f17c77df8643d7a41d6e9159bdae862020-11-25T00:50:47ZengMDPI AGMolecules1420-30492006-11-01111183784810.3390/11110837Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral ActivityMladen MintasErik De ClercqJan BalzariniKrešimir PavelicMarijeta KraljKatja EsterSilvana Raic-MalicBranka ZorcZrinka Rajic3,5-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.http://www.mdpi.com/1420-3049/11/11/837/HydantoinL- and D-amino acidsantiviral activityantitumoral activity. |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Mladen Mintas Erik De Clercq Jan Balzarini Krešimir Pavelic Marijeta Kralj Katja Ester Silvana Raic-Malic Branka Zorc Zrinka Rajic |
| spellingShingle |
Mladen Mintas Erik De Clercq Jan Balzarini Krešimir Pavelic Marijeta Kralj Katja Ester Silvana Raic-Malic Branka Zorc Zrinka Rajic Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity Molecules Hydantoin L- and D-amino acids antiviral activity antitumoral activity. |
| author_facet |
Mladen Mintas Erik De Clercq Jan Balzarini Krešimir Pavelic Marijeta Kralj Katja Ester Silvana Raic-Malic Branka Zorc Zrinka Rajic |
| author_sort |
Mladen Mintas |
| title |
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity |
| title_short |
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity |
| title_full |
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity |
| title_fullStr |
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity |
| title_full_unstemmed |
Hydantoin Derivatives of L- and D-amino acids: Synthesis and Evaluation of Their Antiviral and Antitumoral Activity |
| title_sort |
hydantoin derivatives of l- and d-amino acids: synthesis and evaluation of their antiviral and antitumoral activity |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2006-11-01 |
| description |
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. |
| topic |
Hydantoin L- and D-amino acids antiviral activity antitumoral activity. |
| url |
http://www.mdpi.com/1420-3049/11/11/837/ |
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