A good imitation: Aryl‐1‐indanyl ketones are found to be highly efficient, reversible, cell‐penetrating inhibitors of the human peptidyl prolyl cis/trans isomerase Pin1. Owing to their structure 1, ...they are assumed to mimic the transition state 2 of the enzymatically catalyzed rotation about the imidic peptide bond preceding a proline residue.
The novel 3H-spiro1-benzofuran-2-cyclopentan-3-one skeleton has been made accessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclic benzofuranones 2 and 3, ...respectively. A four-step synthesis to spirocompound 4 is described. The novel spirocyclic benzofuranones display modest to no inhibition of the human peptidyl prolyl cis/trans isomerase Pin1.
The treatment of the 5-(phenylsulfinyl)indoles with trifluoroacetic anhydride in the presence of carbon nucleophiles achieved the title reactions with complete regioselectivity.
The treatment of the ...5-(phenylsulfinyl)indoles with trifluoroacetic anhydride in the presence of carbon nucleophiles achieved the title reactions with complete regioselectivity.
Geschickt imitiert: Aryl‐1‐indanylketone erweisen sich als hocheffiziente, reversible und zellgängige Inhibitoren der humanen Peptidyl‐Prolyl‐cis/trans‐Isomerase Pin1. Aufgrund ihrer Struktur 1 wird ...angenommen, dass sie den Übergangszustand 2 der enzymatisch katalysierten Rotation um die imidische Peptidbindung vor dem Prolin nachahmen.
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