1285534-38-4

Upstream product

• 946-49-6 (E)-4-(4-nitrophenyl)-3-buten-2-one 
• 15753-85-2 (E)-4-(4-aminophenyl)but-3-en-2-one 
• 1122-91-4 4-bromo-benzaldehyde 
• 555-16-8 4-nitrobenzaldehdye 
• 1371578-99-2 (1E,4E)-1-(4-bromophenyl)-5-(4-nitrophenyl)penta-1,4-dien-3-one 

Downstream Products

• 1285534-66-8 C₁₇H₁₄⁽¹²⁵⁾INO 
• 1228557-51-4 2-bromo-N-(4-((1E,4E)-5-(4-bromophenyl)-3-oxopenta-1,4-dienyl)phenyl)acrylamide 

Relevant academic research and scientific papers

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.

Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for ?-Amyloid Plaques

A new and extensive set of dibenzylideneacetone derivatives was synthesized and screened for affinity toward A1-42 aggregates. Structure-activity relationships revealed the binding of dibenzylideneacetones to be affected by various substituents. The introduction of a substituent group in the ortho position reduced or abolished the binding. However, the para position was highly tolerant of sterically demanding substitutions. Three radioiodinated ligands (6, 70, and 71) and two 18F fluoro-pegylated (FPEG) ligands (83 and 85) were prepared, all of which displayed high affinity for A1-42 aggregates (Ki ranging from 0.9 to 7.0 nM). In biodistribution experiments, they exhibited good initial penetration (1.59, 4.68, 4.56, 4.13, and 5.15% ID/g, respectively, at 2 min) of and fast clearance from the brain. Autoradiography with sections of postmortem AD brain and transgenic mouse brain confirmed the high affinity of these tracers. These preliminary results strongly suggest the dibenzylideneacetone structure to be a potential new scaffold for β-amyloid imaging probes.