Design, synthesis and cytotoxicity of novel 3-arylidenones derived from alicyclic ketones

Faculty Mentor(s)

Dr. Kimberly Brien, Hope College
Dr. Vijay Satam, Hope College
Ravi Kumar Bandi, Sambalpur University
Ajaya Kumar Behera, Sambalpur University
Bijay Kumar Mishra, Sambalpur University
Dr. Balaji Babu, Hope College
Matthias Zeller, Youngstown State University
Dr. Moses Lee, Hope College
Hari Pati, Sambalpur University

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As part of the studies in our laboratories aimed at improving the cytotoxicity of combretastatins and chalcones, forty-four novel chalcone analogs derived from alicyclic ketones were designed, synthesized and investigated for cytotoxicity against murine B16 and L1210 cancer cell lines. The chalcone analogs belong to four structurally divergent series, three of which (series g, h and i) contain differently substituted cyclopentanone units and the fourth (series j) contains a 3,3-dimethyl-4-piperidinone moiety. Of these, the chalcone analogs in series j showed potential cytotoxic activity against murine B16 (melanoma) and L1210 (lymphoma) cells. The most active compounds 5j, 11j, 15j, and 12h produced IC50 values from 4.4 to 15 mM against both cell lines. A single crystal X-ray structure analysis and molecular modeling studies confirmed that these chalcones have an E-geometry about the alkene bond and possess a slightly “twisted” conformation similar to that of combretastatin A-4. Compounds 5j, 11j, and 15j did not inhibit tubulin polymerization in A-10 cells suggesting they may have a different mechanism of action.

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