Synthesis and biological activity of N-substituted-tetrahydro-γ-carbolines containing peptide residues

• Nadezhda V. Sokolova,
• Valentine G. Nenajdenko,
• Vladimir B. Sokolov,
• Daria V. Vinogradova,
• Elena F. Shevtsova,
• Ludmila G. Dubova and
• Sergey O. Bachurin

Beilstein J. Org. Chem. 2014, 10, 155–162, doi:10.3762/bjoc.10.13

• Sciences, Severny proezd 1, Chernogolovka, 142432, Russia A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 28, 119991 Moscow, Russian Federation 10.3762/bjoc.10.13 Abstract The synthesis of novel peptide conjugates of N-substituted-tetrahydro-γ-carbolines

• of mitochondria but possessed some inhibitory effect on the mitochondria permeability transition. The original N-substituted-tetrahydro-γ-carbolines containing an terminal alkyne group demonstrated a high prooxidant activity, whereas their conjugates with peptide fragments slightly inhibited both

• autooxidation and the t-BHP-induced lipid peroxidation. Keywords: mitochondrial membrane potential; mitochondrial permeability transition; multicomponent; peptides; tetrahydro-γ-carbolines; Ugi multicomponent reaction; Introduction The design and synthesis of new efficient pharmaceutical drugs for the

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• and tetrahydro-γ-carbolines was performed starting from 2- and 3-alkenylindoles by Pd-catalyzed asymmetric allylic alkylation. A series of (E)-5-substituted indolylcarbonates 33, easily available from the 2-indolylcarbaldehyde, undergo cyclization through a π-allyl-palladium complex by treatment with

• )-configuration of the newly formed stereocenter in enantiomeric excesses up to 97%. Remarkably, the same catalytic system was successfully applied to 3-indolylcarbonates, giving 1-vinyl-tetrahydro-γ-carbolines with high enantiomeric excesses. The intramolecular reaction of 3-(alken-4-yl)indoles 36 was achieved