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Hydantoin derivatives of L- and D-amino acids: synthesis, antiviral and antitumoral activity evaluations

Rajić, Zrinka; Zorc, Branka; Raić-Malić, Silvana; Ester, Katja; Kralj, Marijeta; Pavelić, Krešimir; Balzarini, Jan; De Clercq, Erik; Mintas, Mladen (2006) Hydantoin derivatives of L- and D-amino acids: synthesis, antiviral and antitumoral activity evaluations. Molecules, 11 (11). pp. 837-848. ISSN 1420-3049

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Abstract

3, 5-Disubstituted hydantoin (1, 3-imidazolidinedione) derivatives 5a-h were prepared 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 and antiviral activities. Among all the compounds evaluated, 3-benzhydryl-5-isopropyl hydantoin (5a) showed a weak but selective inhibitory effect against vaccinia virus (EC50 = 16  g/mL ; selectivity index: 25). 3-Cyclohexyl-5-phenyl hydantoin (5g) showed inhibitory activity against cervical carcinoma (HeLa, IC50 = 5.4  M) and breast carcinoma (MCF-7, IC50 = 2  M), but also cytotoxic effects towards human normal fibroblasts (WI 38). On the contrary, the 3-benzhydryl-5-phenyl substituted hydantoin derivative 5h showed moderate inhibitory activity towards HeLa, MCF-7, pancreatic carcinoma (MiaPaCa-2), lung carcinoma (H 460) and colon carcinoma (SW 620) (IC50 = 20 23  M), but no effect on WI 38.

Item Type: Article
Uncontrolled Keywords: Hydantoin ; L- and D-amino acids ; antiviral activity ; antitumoral activity
Subjects: NATURAL SCIENCES > Chemistry
BIOMEDICINE AND HEALTHCARE > Basic Medical Sciences
BIOMEDICINE AND HEALTHCARE > Pharmacy
Divisions: Division of Molecular Medicine
Depositing User: Marijeta Kralj
Date Deposited: 12 Feb 2020 12:29
Last Modified: 24 Feb 2020 15:34
URI: http://fulir.irb.hr/id/eprint/5304
DOI: 10.3390/11110837

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