Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling
α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.
Battenberg, Oliver A.,Nodwell, Matthew B.,Sieber, Stephan A.
experimental part
p. 6075 - 6087
(2011/10/09)
Syntheses of 5-Alkenylpyrimidines by Organotin Reactions
5-Stannylpyrimidines can be prepared from the corresponding bromides by lithiation at -95 deg C and quenching with tributylstannyl chloride.The 5-stannyl-pyrimidine is used in Pd-catalyzed coupling reactions with vinyl bromides.The opposite reaction sequence, i.e.Pd-catalyzed coupling between 5-halopyrimidines and vinyltin derivatives, is also described.Alternatively, the 5-vinylpyrimidines have been obtained by dehydrohalogenation with cesium fluoride and by a modified Wittig reaction. 2-Methylthiopyrimidines are transformed into the 2-methoxy derivatives or 2-pyrimidinones using chloramine-T (CAT) in a simple one-pot synthesis.
Structure Investigations on Products from the Reaction of Organocopper, Organolithium and Organomagnesium Reagents with 2(1H)-Pyrimidinones
Alkyl- and arylcuprates and alkyl- and aryllithium and -magnesium reagents form 3,4- or/and 3,6-adducts with 1-benzyl-2(1H)pyrimidinones.The effect of 5-halo substituents on the reactivity and regioselectivity is reported.Structure analyses were made by NMR spectroscopy.Dehydrogenation gives the conjugated, substituted pyrimidinines.X-Ray crystallographic data for 1-benzyl-5-chloro-4-phenyl-2(1H)-pyrimidinone and its regioisomer 1-benzyl-5-chloro-6-phenyl-2(1H)-pyrimidinone are discussed.
Rise, Frode,Romming, Christian,Undheim, Kjell
p. 459 - 468
(2007/10/02)
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