1422538-40-6Relevant articles and documents
Tetrahydro-β-carboline-based spirocyclic lactam as type II′ β-turn: Application to the synthesis and biological evaluation of somatostatine mimetics
Lesma, Giordano,Cecchi, Roberto,Cagnotto, Alfredo,Gobbi, Marco,Meneghetti, Fiorella,Musolino, Manuele,Sacchetti, Alessandro,Silvani, Alessandra
, p. 2600 - 2610 (2013/05/09)
The synthesis of novel spirocyclic lactams, embodying d-tryptophan (Trp) amino acid as the central core and acting as peptidomimetics, is presented. It relies on the strategic combination of Seebach's self-reproduction of chirality chemistry and Pictet-Spengler condensation as key steps. Investigation of the conformational behavior by molecular modeling, X-ray crystallography, and NMR and IR spectroscopies suggests very stable and highly predictable type II′ β-turn conformations for all compounds. Relying on this feature, we also pursued their application to two potential mimetics of the hormone somatostatin, a pharmaceutically relevant natural peptide, which contains a Trp-based type II′ β-turn pharmacophore.