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

doi:10.1039/c1ob06773g

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 journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	1239-1245
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	6
DOIs	https://doi.org/10.1039/c1ob06773g
State	Published - Feb 14 2012
Externally published	Yes

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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. / Cao, Bin; Wang, Yong; Ding, Kan et al.
In: Organic and Biomolecular Chemistry, Vol. 10, No. 6, 14.02.2012, p. 1239-1245.

Research output: Contribution to journal › Article › peer-review

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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.",

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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

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