کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1362365 981486 2007 14 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Antiproliferative activity of chalcones with basic functionalities
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Antiproliferative activity of chalcones with basic functionalities
چکیده انگلیسی

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.

Basic groups on the chalcone template influenced key physicochemical parameters for antiproliferative activity and possibly, the mode of antiproliferative activity.Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry - Volume 15, Issue 22, 15 November 2007, Pages 7021–7034
نویسندگان
, ,