Synthesis and Structure Activity Relationship Study of N-substituted 3,5-diarylidenepiperidin- 4-ones as Potential Antitumor Agents
Hala Bakr El-Nassan.
A new series of N-substituted diarylidenepiperidin-4-ones was synthesized and screened for their possible anticancer activity
at the NCI Developmental Therapeutic Program. Almost all the synthesized compounds showed more potent antiproliferative activity
than curcumin. The most active compound in this study was 3,5-bis(4-bromobenzylidene)-1-propanoylpiperidin-4-one (8a) with MGMID
GI50, TGI, and LC50 values of 0.35, 1.62 and 9.12 µM, respectively. Compound 8a displayed broad spectrum antiproliferative
activity with GI50 values below 1 µM in 81% of the tested cell lines and was found to be two folds more potent than EF-24. A detailed
study of the structure activity relationship of the N-substitution was also described.
Keywords: Curcumin derivatives, antitumor, structure-activity relationship, 3, 5-diarylidene-4-piperidones.
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