Synthetic chalcone derivatives as inhibitors of cathepsins K and B, and their cytotoxic evaluation.

Autor: Ramalho SD; Department of Chemistry, State University of Goiás, 495, Anápolis, GO, Brazil; Department of Chemistry, Federal University of São Carlos, 13565-905, São Carlos, SP, Brazil., Bernades A, Demetrius G, Noda-Perez C, Vieira PC, Dos Santos CY, da Silva JA, de Moraes MO, Mousinho KC
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2013 Nov; Vol. 10 (11), pp. 1999-2006.
DOI: 10.1002/cbdv.201200344
Abstrakt: A series of chalcone derivatives, 1-15, were prepared by Claisen-Schmidt condensation and evaluated for their cytotoxicities on tumor cell lines and also against proteolytic enzymes such as cathepsins B and K. Of the compounds synthesized, (E)-3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one (12), (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (13), (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (14), and (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one (15) showed significant cytotoxicities. The most effective compound was 15, which showed high cytotoxic activity with an IC50 value lower than 1 μg/ml, and no selectivity on the tumor cells evaluated. Substituents at C(4) of ring B were found to be essential for cytotoxicity. In addition, it was also demonstrated that some of these chalcones are moderate inhibitors of cathepsin K and have no activity against cathepsin B.
(Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.)
Databáze: MEDLINE
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