Antiproliferative activity of β-hydroxy- β-arylalkanoic acids
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Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal ...importance as lipophilicity.
Кључне речи:
β-hydroxy-β-arylalkanoic acids / Antiproliferative activity / Human dedifferentiate cells / QSAR / Reformatsky reaction / Antiproliferativna aktivnostИзвор:
International Journal of Molecular Sciences, 2007, 8, 3, 214-228Издавач:
- MDPI
Финансирање / пројекти:
- Синтеза, карактеризација и активност органских и координационих једињења и њихова примена у (био)нанотехнологији (RS-MESTD-MPN2006-2010-142010)
DOI: 10.3390/i8030214
ISSN: 1661-6596; 1422-0067
WoS: 000245396500004
Scopus: 2-s2.0-34047235830
Институција/група
IHTMTY - JOUR AU - Dilber, Sanda P. AU - Žižak, Željko AU - Stanojković, Tatjana AU - Juranić, Zorica AU - Drakulić, Branko PY - 2007 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4305 AB - Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal importance as lipophilicity. PB - MDPI T2 - International Journal of Molecular Sciences T1 - Antiproliferative activity of β-hydroxy- β-arylalkanoic acids VL - 8 IS - 3 SP - 214 EP - 228 DO - 10.3390/i8030214 ER -
@article{ author = "Dilber, Sanda P. and Žižak, Željko and Stanojković, Tatjana and Juranić, Zorica and Drakulić, Branko", year = "2007", abstract = "Article describes the synthesis of fifteen β-hydroxy- β-arylalkanoic acids by Reformatsky reaction using the 1-ethoxyethyl-2- bromoalkanoates, aromatic or cycloalkyl ketones or aromatic aldehydes. The short survey of previously reported synthetic procedures for title compounds, is given. The majority of obtained compounds exert antiproliferative activity in vitro toward human: HeLa, Fem-X cells, K562, and LS174 cells, having IC 50 values from 62.20 to 205 μM. The most active compound is 3-OH-2,2-di-Me-3-(4-biphenylyl)-butanoic acid, having the IC 50 value 62.20 μM toward HeLa cells. Seven examined compounds did not affect proliferation of healthy human blood peripheral mononuclear cells (PBMC and PBMC+ PHA), IC 50 > 300 μM. The preliminary QSAR results show that estimated lipophilicity of compounds influences their antiproliferative activity in the first place. The ability of dehydration, and the spatial arrangement of hydrophobic portion, HBD and HBA in molecules are has almost equal importance as lipophilicity.", publisher = "MDPI", journal = "International Journal of Molecular Sciences", title = "Antiproliferative activity of β-hydroxy- β-arylalkanoic acids", volume = "8", number = "3", pages = "214-228", doi = "10.3390/i8030214" }
Dilber, S. P., Žižak, Ž., Stanojković, T., Juranić, Z.,& Drakulić, B.. (2007). Antiproliferative activity of β-hydroxy- β-arylalkanoic acids. in International Journal of Molecular Sciences MDPI., 8(3), 214-228. https://doi.org/10.3390/i8030214
Dilber SP, Žižak Ž, Stanojković T, Juranić Z, Drakulić B. Antiproliferative activity of β-hydroxy- β-arylalkanoic acids. in International Journal of Molecular Sciences. 2007;8(3):214-228. doi:10.3390/i8030214 .
Dilber, Sanda P., Žižak, Željko, Stanojković, Tatjana, Juranić, Zorica, Drakulić, Branko, "Antiproliferative activity of β-hydroxy- β-arylalkanoic acids" in International Journal of Molecular Sciences, 8, no. 3 (2007):214-228, https://doi.org/10.3390/i8030214 . .