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Synthesis of 4′‐Hydroxy‐3′‐piperidinomethylchalcone Derivatives and Their Cytotoxicity Against PC‐3 Cell Lines
Author(s) -
Gul Halise I.,
Yerdelen Kadir O.,
Gul Mustafa,
Das Umashankar,
Pandit Bulbul,
Li PuiKai,
Secen Hasan,
Sahin Fikrettin
Publication year - 2007
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200600072
Subject(s) - cytotoxicity , chalcone , chemistry , stereochemistry , aryl , chemical synthesis , cell culture , in vitro , mannich base , potency , cytotoxic t cell , biochemistry , organic chemistry , biology , alkyl , genetics
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 (IC 50 = 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.