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Molecular Hybridization-Guided Construction of Convolutamydine A-fused β-Ionone Scaffolds and their Biological Evaluation for Anticancer Activities

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Described herein is a facile and efficient methodology toward the synthesis of novel convolutamydine A-incorporated β-ionone scaffold 3 from an Aldol addition event of β-ionone to isatins via enamine Et2NH… Click to show full abstract

Described herein is a facile and efficient methodology toward the synthesis of novel convolutamydine A-incorporated β-ionone scaffold 3 from an Aldol addition event of β-ionone to isatins via enamine Et2NH catalysis. Products featuring a quaternary carbon center were smoothly obtained in good yields (up to 96% yield). This protocol also represents the first construction of ionone skeleton-fused oxindole molecules, thus leading to new knowledge in the fields of both molecular complexity and diversity-oriented synthesis and the lead compound discovery. Furthermore, their biological activities against human leukemia cells K562 have been preliminarily demonstrated by in vitro assays. The results demonstrated that most of these compounds obtained by this protocol showed comparable with or even much better than the positive control of Cisplatin.

Keywords: convolutamydine; molecular hybridization; ionone; guided construction; hybridization guided

Journal Title: Journal of Heterocyclic Chemistry
Year Published: 2018

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