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

29 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 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Publisher link

10.1039/c1ob06773g

Find It

Find It at U of M Libraries

Cite this

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

@article{b30f442c1477445c9eeae03e8a2c0e20,

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

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.",

author = "Bin Cao and Yong Wang and Kan Ding and Nouri Neamati and Long, \{Ya Qiu\}",

year = "2012",

month = feb,

day = "14",

doi = "10.1039/c1ob06773g",

language = "English (US)",

volume = "10",

pages = "1239--1245",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "6",

}

TY - JOUR

T1 - Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen-Schmidt condensation, displaying diverse biological activities as curcumin analogues

AU - Cao, Bin

AU - Wang, Yong

AU - Ding, Kan

AU - Neamati, Nouri

AU - Long, Ya Qiu

PY - 2012/2/14

Y1 - 2012/2/14

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84862938231

UR - https://www.scopus.com/pages/publications/84862938231#tab=citedBy

U2 - 10.1039/c1ob06773g

DO - 10.1039/c1ob06773g

M3 - Article

C2 - 22179573

AN - SCOPUS:84862938231

SN - 1477-0520

VL - 10

SP - 1239

EP - 1245

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 6

ER -

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

Abstract

UN SDGs

Publisher link

Find It

Other files and links

Fingerprint

Cite this