1229936-44-0Relevant articles and documents
Enantioselective Synthesis of Pyrrolopyrimidine Scaffolds through Cation-Directed Nucleophilic Aromatic Substitution
Cardenas, Mariel M.,Toenjes, Sean T.,Nalbandian, Christopher J.,Gustafson, Jeffrey L.
, p. 2037 - 2041 (2018)
The catalytic enantioselective synthesis of 3-aryl-substituted pyrrolopyrimidines (PPYs), a common motif in drug discovery, is achieved through a kinetic resolution via quaternary ammonium salt-catalyzed nucleophilic aromatic substitution (SNAr). Both enantioenriched products and starting materials can be functionalized with no observed racemization to give enantiodivergent access to diverse chiral analogues of an important class of kinase inhibitor. One of the compounds was found to be a potent and selective inhibitor of breast tumor kinase.
Optochemical control of transcription by the use of 7-deaza-adenosine-based diarylethenes
Büllmann, Simon M.,Kolmar, Theresa,Slawetzky, Philip,Wald, Simon,J?schke, Andres
, p. 6596 - 6599 (2021)
Out of nine different 7-deaza-adenosine diarylethenes, we identified a high-performance photoswitch, suitable for the synthesis of photochromic DNA. By using solid phase synthesis, a photoresponsive T7 promotor was generated which allowed reversibly modulating the rate of enzymatic RNA synthesisin vitro.
The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
Sarter, Christopher,Heimes, Michael,J?schke, Andres
supporting information, p. 1103 - 1110 (2016/07/06)
Diarylethenes are an important class of reversible photoswitches and often claimed to require two alkyl substituents at the carbon atoms between which the bond is formed or broken in the electrocyclic rearrangement. Here we probe this claim by the synthesis and characterization of four pairs of deazaadenine-based diarylethene photoswitches with either one or two methyl groups at these positions. Depending on the substitution pattern, diarylethenes with one alkyl group can exhibit significant photochromism, but they generally show poor stability towards extended UV irradiation, low thermal stability, and decreased fatigue resistance. The results obtained provide an important direction for the design of new efficient DNA photoswitches for the application in bionanotechnology and synthetic biology.