17191-43-4Relevant articles and documents
BICYCLIC COMPOUNDS AND METHODS FOR THEIR USE IN TREATING PITT HOPKINS SYNDROME
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Page/Page column 41; 42, (2021/04/30)
Embodiments of this invention provide compounds, compositions, methods, and uses for therapeutic diketopiperazines, including cyclic G-2-Allyl Proline and other cyclic Glycyl Proline compounds to treat Pitt Hopkins Syndrome and symptoms thereof, as well a
The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement
Szczes?niak, Piotr,Pieczykolan, Micha?,Stecko, Sebastian
, p. 1057 - 1074 (2016/02/19)
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
Foldamer-mediated remote stereocontrol: >1,60 asymmetric induction
Byrne, Liam,Sola, Jordi,Boddaert, Thomas,Marcelli, Tommaso,Adams, Ralph W.,Morris, Gareth A.,Clayden, Jonathan
supporting information, p. 151 - 155 (2014/01/17)
An N-terminal L-α-methylvaline dimer induces complete conformational control over the screw sense of an otherwise achiral helical peptide foldamer formed from the achiral quaternary amino acids Aib and Ac6c. The persistent right-handed screw-sense preference of the helix enables remote reactive sites to fall under the influence of the terminal chiral residues, and permits diastereoselective reactions such as alkene hydrogenation or iminium ion addition to take place with 1,16-, 1,31-, 1,46- and even 1,61-asymmetric induction. Stereochemical information may be communicated in this way over distances of up to 4 nm. Reaction at a distance: By inducing a quantitative, persistent preference for right-handed helicity, chirality at one end of an otherwise achiral helical molecule is able to control the stereoselectivity of reactions at sites located up to 60 bonds away, shattering previous records for remote stereochemical control. Copyright