71433-00-6Relevant academic research and scientific papers
Regioselective synthesis of inhibitors of histone acetyl transferase covalently linking spermidine to the S-terminus of coenzyme A and fragments.
Roblot, Georges,Wylde, Renee,Martin, Aimee,Parello, Joseph
, p. 6381 - 6398 (1993)
The reaction of a bromoacetylthioester BrCH2CO-S-R (R radical in the coenzyme A series) with spermidine (Spd) derivatives is investigated and it is established that the adduct SpdCOCH2-S-R 1 is the product of the reaction.Parallel studies with model compounds show that this is a general reaction of bromoacetylthioesters.The synthesis of analogs of 1 is described and they correspond to inhibitors of the histone acetyltransferase. Key words: spermidine, coenzyme A, cysteamine, β-aletheine, enzyme inhibitors.
Fluorination of sulfanyl amides using difluoroiodoarene reagents
Motherwell, William B.,Greaney, Michael F.,Edmunds, Jeremy J.,Steed, Jonathan W.
, p. 2816 - 2826 (2007/10/03)
A range of sulfur-containing amides have been fluorinated with the hypervalent iodine difluoride reagents 1, and two principal reaction pathways identified. Cephalosporin esters 2 having a heteroatom in the α-position to sulfur undergo fluorination in DCM with cleavage of the carbon-sulfur bond to form novel fluorinated β-lactams 4. Sulfides with electron-withdrawing groups in the α-position undergo α-fluorination in a process analogous to the classical Pummerer reaction. This Fluoro-Pummerer reaction has been exemplified for a range of simple α-phenylsulfanylacetamides 14-19. When β-hydrogens are present in the substrate a different route is followed, with deprotonation by basic fluoride taking place to yield vinyl sulfides 41-43. When an excess of the fluorinating reagent is used these vinyl sulfides can undergo further reaction in a novel tandem Pummerer-Additive-Pummerer process to yield α,β-difluoro sulfides 45-47.
