26159-26-2

Basic information

• Product Name: 1,5-bis(3-pyridyl)-1,4-pentadiene-3-one
• CAS NO: 26159-26-2
• Molecular Weight: 236.273
• Mol File: 26159-26-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,5-bis(3-pyridyl)-1,4-pentadiene-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-bis(3-pyridyl)-1,4-pentadiene-3-one(26159-26-2)
• EPA Substance Registry System: 1,5-bis(3-pyridyl)-1,4-pentadiene-3-one(26159-26-2)

Safety Data

• Hazardous Substances Data: 26159-26-2(Hazardous Substances Data)

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 542-05-2 acetonedicarboxylic acid 
• 67-64-1 acetone 
• 1475-91-8 [3-(diethoxy-phosphoryl)-2-oxo-propyl]-phosphonic acid diethyl ester 

Relevant articles and documents

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

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. The Royal Society of Chemistry 2012.

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Anti-oxidant activities of curcumin and related enones

The natural product curcumin (diferuloylmethane, 1,7-bis(4-hydroxy-3- methoxyphenyl)-1,6-heptadiene-3,5-dione), obtained from the spice turmeric, exhibits numerous biological activities including anti-cancer, anti-inflammatory, and anti-angiogenesis activities. Some of these biological activities may derive from its anti-oxidant properties. There are conflicting reports concerning the structural/electronic basis of the anti-oxidant activity of curcumin. Curcumin is a symmetrical diphenolic dienone. A series of enone analogues of curcumin were synthesized that included: (1) curcumin analogues that retained the 7-carbon spacer between the aryl rings; (2) curcumin analogues with a 5-carbon spacer; and (3) curcumin analogues with a 3-carbon spacer (chalcones). These series included members that retained or were devoid of phenolic groups. Anti-oxidant activities were determined by the TRAP assay and the FRAP assay. Most of the analogues with anti-oxidant activity retained the phenolic ring substituents similar to curcumin. However, a number of analogues devoid of phenolic substituents were also active; these non-phenolic analogues are capable of forming stable tertiary carbon-centered radicals.