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Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen–Schmidt condensation, displaying diverse biological activities as curcumin analogues?

Organic & Biomolecular Chemistry Pub Date: 2011-11-17 DOI: 10.1039/C1OB06773G

Abstract

An efficient and easy procedure to synthesize the pyridinyl analogues of dibenzylideneacetone (pyr-dba) was developed by the condensation of substituted nicotinaldehyde and acetone in the presence of K₂CO₃ in toluene-EtOH-H₂O solvent system. Structurally diverse pyr-dba, including quinolinyl dba, can be prepared conveniently in moderate to excellent yields under mild conditions with this method. The resulting pyr-dba functioned as the enone analogs of curcumin and efficiently inhibited the activation of NF-κB and the growth of colorectal carcinoma HCT116 p53+/+ cells as well as the HIV-1 IN-LEDGF/p75 interaction.

Graphical abstract: Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen–Schmidt condensation, displaying diverse biological activities as curcumin analogues

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Organic & Biomolecular Chemistry

Journal Name：Organic & Biomolecular Chemistry

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