27911-82-6

Basic information

• Product Name: 1-(3-nitro-phenyl)-5-phenyl-penta-1,4-dien-3-one
• Synonyms: 1-(3-nitro-phenyl)-5-phenyl-penta-1,4-dien-3-one
• CAS NO: 27911-82-6
• Molecular Weight: 279.295
• Mol File: 27911-82-6.mol

Chemical Properties

• CAS DataBase Reference: 1-(3-nitro-phenyl)-5-phenyl-penta-1,4-dien-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-nitro-phenyl)-5-phenyl-penta-1,4-dien-3-one(27911-82-6)
• EPA Substance Registry System: 1-(3-nitro-phenyl)-5-phenyl-penta-1,4-dien-3-one(27911-82-6)

Safety Data

• Hazardous Substances Data: 27911-82-6(Hazardous Substances Data)

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 1371579-38-2 2-bromo-N-(3-((1E,4E)-3-oxo-5-phenylpenta-1,4-dienyl)phenyl)acrylamide 

Relevant articles and documents

Design, synthesis and biological evaluation of hybrid molecules containing conjugated styryl ketone and α-bromoacryloyl moieties

There was a major interest in the last years in the design of anticancer agents containing the 1,5-diaryl-3-oxo-1,4-pentadienyl system. The modification of this pharmacophore by the introduction of an additional Michael acceptor represents a strategy to obtain novel potential antiproliferative agents. In a continuing study of hybrid compounds containing the α-bromoacryloyl moiety as potential anticancer drugs, we synthesized two novel series of hybrids 3a-i and 4a-i, in which this moiety was linked to the 1,5-diaryl-1,4-pentadien-3-one system. Many of the conjugates prepared (3b, 3c and 3g) demonstrated pronounced antiproliferative activity against five cancer cell lines, being more active than the reference compound Melphalan. Compounds 3e and 4b were also examined for their effects on the cell cycle progression of K562 cells. The detection of a sub-G1 peak upon incubation with these compounds suggested that 3e and 4b also exert their growth inhibiting effects by induction of apoptosis.

CHLOROSULFONATION OF α,β-UNSATURATED ARYLIDENE KETONES

2-Thienylideneacetone (4), and the benzylidene derivatives of ethyl methyl ketone (19) and diethyl ketone (20) were reacted with excess chlorosulfonic acid to give the thienylidene 5,β-disulfonyl chloride (5) and the styrene disulfonyl chlorides (21 and 22).These were characterized by preparation of the sulfonamides (6-9, 23 and 24) required for screening as pest control agents.Benzylidene acetone (1) was condensed with aryl aldehydes to give the corresponding 1,5-diaryl-1,4-dien-3-ones (25-28), but the condensation failed with p-anisaldehyde and o-vanillin.Attempted chlorosulfonation of compounds (25 and 28) was unsuccessful and the products could not be characterised as sulfonamide derivatives.The 1H NMR spectra of selected compounds are briefly discussed.Key words: Chlorosulfonation of α,β-unsaturated arylidene ketones; thienylidene 5,β-disulfonyl chloride; styrene disulfonyl chlorides.