Abstract: Article describes the synthesis of fifteen β-hydroxy-β-arylalkanoic acids byReformatsky reaction using the 1-ethoxyethyl-2-bromoalkanoates, aromatic or cycloalkylketones or aromatic aldehydes. The short survey of previously reported synthetic proceduresfor title compounds, is given. The majority of obtained compounds exert antiproliferativeactivity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC50values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC50 value 62.20 μM toward HeLa cells. Sevenexamined compounds did not affect proliferation of healthy human blood peripheralmononuclear cells (PBMC and PBMC PHA), IC50 > 300 μM. The preliminary QSARresults show that estimated lipophilicity of compounds influences their antiproliferativeactivity in the first place. The ability of dehydration, and the spatial arrangement ofhydrophobic portion, HBD and HBA in molecules are has almost equal importance aslipophilicity.
Keywords: β-hydroxy-β-arylalkanoic acids; Reformatsky reaction; antiproliferative activity; human dedifferentiate cells; QSAR
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Dilber, S.P.; Žižak, Ž.S.; Stanojković, T.P.; Juranić, Z.D.; Drakulić, B.J.; Juranić, I.O. Antiproliferative Activity of β-Hydroxy-β-Arylalkanoic Acids. Int. J. Mol. Sci. 2007, 8, 214-228.
Dilber SP, Žižak ŽS, Stanojković TP, Juranić ZD, Drakulić BJ, Juranić IO. Antiproliferative Activity of β-Hydroxy-β-Arylalkanoic Acids. International Journal of Molecular Sciences. 2007; 8(3):214-228.
Dilber, Sanda P.; Žižak, Željko S.; Stanojković, Tatjana P.; Juranić, Zorica D.; Drakulić, Branko J.; Juranić, Ivan O. 2007. "Antiproliferative Activity of β-Hydroxy-β-Arylalkanoic Acids." Int. J. Mol. Sci. 8, no. 3: 214-228.