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

Bin Cao, Yong Wang, Kan Ding, Nouri Neamati, Ya Qiu Long

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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 K 2CO 3 in toluene-EtOH-H 2O 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.

Original languageEnglish (US)
Pages (from-to)1239-1245
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number6
DOIs
StatePublished - Feb 14 2012

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