Design, Synthesis and Cytotoxicity of Novel Chalcone Analogs Derived From 1-Cyclohexylpyrrolidin-2-one and 2,3-Dihydrobenzo[f]chromen-1-one

Document Type


Publication Date



The authors thank Conjura Pharmaceuticals, LLC for support. Support from the Department ofChemistry, Sambalpur University for providing facilities for research is also acknowledged. The X-ray diffractometer at Youngstown State University was funded by NSF Grant 0087210, Ohio Board of Regents Grant CAP-491, and by Youngstown State University. Support from the President's Council Excellence award is acknowledged (SLM).


Two divergent series of novel chalcone analogs, one derived from 1-cyclohexylpyrrolidin-2-one and the other derived from 1-benzo[f]chromanone, were designed, synthesized and evaluated for cytotoxicity against two murine cancer cell lines. Two 1-benzo[f]chromanone analogs, 4g and 4j yielded moderate toxicity against both melanoma B16 and lymphoma L1210 cell lines with IC50 values between the range of 5 and 6?mu M. With an IC50 value of 3.4?mu M, compound 4g was also active against human MDA-MB-435 melanoma cells. X-ray structures of the beta-hydroxy ketone product (4a) and the a,beta-unsaturated ketone (4h) were collected, and confirm the syn-configuration between the carbonyl moiety and the beta-vinylic proton in 4h. X-ray structures of two 1-cyclohexylpyrrolidin-2-one derivatives were also obtained, and both showed an E-configuration for the double bond.