192067-89-3

Upstream product

• 13610-02-1 1-phenoxy-2-propyne 
• 134136-83-7 1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)propan-1-one 
• 618359-62-9 4-O-tert-butyldimethylsilyloxyphenyl-1-propanol 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-96-7 propargyl bromide 
• 70-70-2 4-hydroxypropiophenone 
• 108-95-2 phenol 

Downstream Products

• 70-70-2 4-hydroxypropiophenone 

Relevant academic research and scientific papers

Unambiguous Identification of β-Tubulin as the Direct Cellular Target Responsible for the Cytotoxicity of Chalcone by Photoaffinity Labeling

Chalcone is a simple and potentially privileged structure in medicinal chemistry with a diverse repertoire of biological activities, among which cytotoxicity is of particular interest. The sharp structure–activity relationship (SAR) for chalcone's cytotoxicity suggests structure-specific target interactions. Despite the numerous putative targets proposed, evidence for direct target interactions in cells is unavailable. In this study, guided by the sharp cytotoxic SAR, we developed a cytotoxic chalcone-based photoaffinity labeling (PAL) probe, (E)-3-(3-azidophenyl)-1-[3,5-dimethoxy-4-(prop-2-yn-1-yloxy)phenyl]-2-methylprop-2-en-1-one (C95; IC50: 0.38±0.01 μm), along with two structurally similar non-cytotoxic probes. These probes were used to search for the direct cellular target responsible for chalcone's cytotoxicity through intact cell-based PAL experiments, in which β-tubulin was identified to specifically interact with the cytotoxic probe (i.e., C95) but not the non-cytotoxic probes. A set of phenotypical and biochemical assays further reinforced β-tubulin as the cytotoxic target of chalcones. Peptide mass quantitation by mass spectrometric analysis revealed one peptide potentially labeled by C95, providing information on chalcone's binding site on β-tubulin.

Palladium-catalyzed cleavage of O/N-propargyl protecting groups in aqueous media under a copper-free condition

(Figure presented) A copper-free palladium-mediated cleavage of O/N-propargyl bonds in aqueous media has been investigated, affording a mild and convenient method for the deprotection of phenols and anilines. The methodology could be utilized for the selective removal of propargyl groups from aryl ethers and amines without affecting a variety of unprotected functional groups present in the substrates. The mechanism and scope of the reaction is discussed.