Background:
A series of novel 5-substituted benzylidene rhodanine derivatives using four different amines
were designed based on our previously developed CoMSIA (Comparative molecular similarity indices analysis) model
for the anticancer activity.
Method:
The designed rhodanines were synthesised via dithiocarbamate formation, cyclization and Knoevenagel condensation. The synthesized compounds were analyzed by spectral studies to confirm their structures.
Result:
The synthesized rhodanines were investigated for in vitro anticancer activities and the analogs have displayed
mild to significant cytotoxicity against MCF-7 breast cancer cells. The compounds with benzyloxy substitution at the fifth
position of rhodanine ring (Compounds 20, 33 and 38) system showed significant cytotoxic activity against MCF-7 cells.
CoMSIA, a three-dimensional quantitative structure-activity relationship (3D-QSAR) technique was accomplished to
elucidate structure-activity relationships.
Conclusions:
Based on the information derived from CoMSIA contour plots, some key features for increasing the activity
of compounds have been identified and have been used to design new anti-cancer agents. The present developed CoMSIA
model displayed good external predictability r2pred of 0.841 and good statistical robustness.
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