Beilstein J. Org. Chem.2021,17, 1453–1463, doi:10.3762/bjoc.17.101
cancer cells.
Keywords: γ-carboline; cascade reaction; cell uptake; cytotoxicity; fluorescence; Introduction
Carbolines are privileged aza-heterocycles found in the core of several natural and synthetic compounds and are known for their biological applications. Among the four different isomers, 9H
shown promising biological activities in preclinical and clinical studies (Figure 1) [2][3][4][5][6].
The pyrimidine-γ-carboline alkaloid ingenine B (isolated from an Indonesian sponge) exhibits a pronounced cytotoxicity against a murine lymphoma cell line [7] and several isocanthine analogs are
active tetrahydro-γ-carboline derivatives [13][14]. A systematic assessment of the above Graebe–Ullmann and Fischer synthesis protocols revealed that these reactions are associated with i) low product yield, ii) limited scope including the use of a very specific set of substrates, and iii) involvement of
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Graphical Abstract
Figure 1:
Selected examples of compounds containing the γ-carboline core.
Beilstein J. Org. Chem.2014,10, 155–162, doi:10.3762/bjoc.10.13
has been performed using the sequence of the Ugi multicomponent reaction and Cu(I)-catalyzed click chemistry. The effect of obtained γ-carboline–peptide conjugates on the rat liver mitochondria was evaluated. It was found that all compounds in the concentration of 30 µM did onot induce depolarization
view, mitochondria and the MPT process are very attractive targets for the search of new neuroprotective agents [4][5].
Several promising mitochondria-targeting neuroprotectors have been reported in the literature. Thus, the antihistaminic drug dimebon [6][7], which relates to tetrahydro-γ-carboline