Issue 6, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Bin Cao,a   Yong Wang,a   Kan Ding,a   Nouri Neamatib  and  Ya-Qiu Long*a  

* Corresponding authors

a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, China
E-mail: yqlong@mail.shcnc.ac.cn
Fax: 86-21-50807088
Tel: 86-21-50806876

b Department of Pharmacology and Pharmaceutical Sciences, School of Pharmacy, University of Southern California, 1985 Zonal Avenue, Los Angeles, CA, USA

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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Article information

DOI
https://doi.org/10.1039/C1OB06773G
Article type
Paper
Submitted
21 Oct 2011
Accepted
04 Nov 2011
First published
17 Nov 2011

Org. Biomol. Chem., 2012,10, 1239-1245

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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

B. Cao, Y. Wang, K. Ding, N. Neamati and Y. Long, Org. Biomol. Chem., 2012, 10, 1239 DOI: 10.1039/C1OB06773G

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