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|Title:||Antiproliferative activity of chalcones with basic functionalities|
|Authors:||Liu, X. |
Chalcones with basic functionalities
|Citation:||Liu, X., Go, M.-L. (2007). Antiproliferative activity of chalcones with basic functionalities. Bioorganic and Medicinal Chemistry 15 (22) : 7021-7034. ScholarBank@NUS Repository.|
|Abstract:||A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the β carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the β carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but still maintained a good activity profile with IC50 < 10 μM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. © 2007 Elsevier Ltd. All rights reserved.|
|Source Title:||Bioorganic and Medicinal Chemistry|
|Appears in Collections:||Staff Publications|
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