193140-68-0Relevant academic research and scientific papers
Biomimetic transamination of α-keto perfluorocarboxylic esters. An efficient preparative synthesis of β,β,β-trifluoroalanine
Soloshonok, Vadim A.,Kukhar, Valery P.
, p. 8307 - 8314 (1997)
An efficient large-scale preparative synthesis of biologically interesting β,β,β-trifluoroalanine through the biomimetic transamination of the ethyl trifluoropyruvate has been developed. The azomethine-azomethine isomerization of the N-(1-phenyl)ethylimine of ethyl trifluoropyruvate to the N-(l-phenyl)ethylidene alanine ethyl ester, a key stage of the process, was found to occur under the mild reaction conditions, in a triethylamine solution at rt. The proposed working mechanistic rationale accounting for the easiness of the isomerization and its stereochemical outcome, involves unusual non-asymmetric [1,5]-proton shift transfer from the methine carbon to the enolate oxygen.
Structure-Activity Relationships of Organofluorine Inhibitors of β-Amyloid Self-Assembly
Toeroek, Bela,Sood, Abha,Bag, Seema,Kulkarni, Aditya,Borkin, Dmitry,Lawler, Elizabeth,Dasgupta, Sujaya,Landge, Shainaz,Abid, Mohammed,Zhou, Weihong,Foster, Michelle,Levine, Harry,Toeroek, Marianna
experimental part, p. 910 - 919 (2012/08/28)
A broad group of structurally diverse small organofluorine compounds were synthesized and evaluated as inhibitors of β-amyloid (Aβ) self-assembly. The main goal was to generate a diverse library of compounds with the same functional group and to observe general structural features that characterize inhibitors of Aβ oligomer and fibril formation, ultimately identifying structures for further focused inhibitor design. The common structural motifs in these compounds are CF3-C-OH and CF3-C-NH groups that were proposed to be binding units in our previous studies. A broad range of potential small-molecule inhibitors were synthesized by combining various carbocyclic and heteroaromatic rings with an array of substituents, generating a total of 106 molecules. The compounds were tested by standard methods such as thioflavin-T fluorescence spectroscopy for monitoring fibril formation, biotinyl Aβ1-42 single-site streptavidin-based assays for observing oligomer formation, and atomic force microscopy for morphological studies. These assays revealed a number of structures that show significant inhibition against either Aβ fibril or oligomer formation. A detailed analysis of the structure-activity relationship of anti-fibril and -oligomer properties is provided. These data present further experimental evidence for the distinct nature of fibril versus oligomer formation and indicate that the interaction of the Aβ peptide with chiral small molecules is not stereospecific in nature.
Triflic acid-catalyzed highly stereoselective friedel-crafts aminoalkylation of indoles and pyrroles
Abid, Mohammed,Teixeira, Liliana,Toeroek, Bela
supporting information; experimental part, p. 933 - 935 (2009/04/07)
A simple and efficient synthesis to both enantiomers of highly enantiomerically enriched α-trifluoromethyl-α-(heteroaryl)-glycine derivatives via highly stereoselective aminoalkylation of indoles and pyrroles is described. The triflic acid-catalyzed react
