Synthesis of 4′-Hydroxy-3′-piperidinomethylchalcone Derivatives and Their Cytotoxicity Against PC-3 Cell Lines

A new series of mono Mannich bases of 4′‐hydroxychalcones 2a–e carrying a variety of aryl groups was synthesized and the in vitro cytotoxic activities of the new compounds were screened against PC‐3 cell lines. Bioactivities of 2a–e, which are reported for the first time in this study, were compared...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2007-04, Vol.340 (4), p.195-201
Main Authors: Gul, Halise I., Yerdelen, Kadir O., Gul, Mustafa, Das, Umashankar, Pandit, Bulbul, Li, Pui-Kai, Secen, Hasan, Sahin, Fikrettin
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Cell Survival - drug effects
Chalcone
Chalcones - chemical synthesis
Chalcones - pharmacology
Chemical Phenomena
Chemistry, Physical
Cytotoxicity
Humans
Indicators and Reagents
Mannich base
Mannich Bases - chemical synthesis
Mannich Bases - pharmacology
PC-3 cells
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Synthesis
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Summary:A new series of mono Mannich bases of 4′‐hydroxychalcones 2a–e carrying a variety of aryl groups was synthesized and the in vitro cytotoxic activities of the new compounds were screened against PC‐3 cell lines. Bioactivities of 2a–e, which are reported for the first time in this study, were compared against their precursor 4′‐hydroxychalcones 1a–e. Compound 2b was found to be the most potent (IC50 = 3.7 μM) among the compounds synthesized. In addition, the compounds 1a–c and 2d showed moderate cytotoxicity. Incorporation of the 3′‐piperidinomethyl group in 1b and 1d raised the potency by 1.68 and 2.19 times respectively and, therefore, seemed to be a noteworthy molecular modification. Correlations were noted between cytotoxicity and one or more physiochemical constants of the aryl ring as well as log P values for the compounds 2a–e. The significant improvement of cytotoxicity of 2b, 2d, and 2e against PC‐3 cell lines compared with their chalcone precursors suggests that the incorporation of a piperidinomethyl group is a useful molecular modification and further development of these compounds as candidate cytotoxic agents may be warranted.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.200600072