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Development of Novel Rhodanine Analogs as Anticancer Agents: Design, Synthesis, Evaluation and CoMSIA Study

Author(s):

Uma Krithika, Prabitha P, Subhankar P. Mandal, Yuvaraj S, Priya D, Ashish D Wadhwani and B. R. Prashantha Kumar*   Pages 1 - 14 ( 14 )

Abstract:


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.

Conclusion: 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.

Keywords:

Rhodanine, Knoevenagel condensation, MCF-7 cells, anticancer activity, CoMSIA, 3D QSAR.

Affiliation:

Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015, Department of Biotechnology, JSS College of Pharmacy, Ootacamund 643 001, India; JSS Academy of Higher Education & Research, Mysuru, Department of Pharmaceutical Chemistry, JSS College of Pharmacy, Mysuru 570 015



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