TY  - JOUR
U1  - Wissenschaftlicher Artikel
A1  - Schulze, Wolfram
A1  - Zimmer, Anne
A1  - Neudörfl, Jörg‐Martin
A1  - Dato, Florian M.
A1  - Sommerfeld, Paul
A1  - Pietsch, Markus
A1  - Derondeau, Henrieta
A1  - Gaida, Florian
A1  - Riedle, Eberhard
A1  - Griesbeck, Axel G.
T1  - Photodecarboxylative Ring Annulation of α‐ and β‐Functionalized Phthaloyl‐GABA Derivatives: Bioactive Pyrroloisoindolinones with High Quantum Efficiency
JF  - ChemPhotoChem
N2  - AbstractThe triplet‐sensitized (by the solvent acetone) as well as the direct (λex=300–320 nm) photochemical decarboxylation of N‐phthaloylated γ‐aminobutyric acid (GABA) derivatives are versatile and high‐yielding routes to benzopyrrolizidines via intramolecular electron transfer initiated decarboxylation followed by radical coupling. The ß‐mono‐ and ß,ß'‐disubstituted N‐phthaloyl GABA derivatives 7 a–7 g, respectively, were applied as substrates. Decarboxylative photocyclization yielded hydroxy benzopyrrolizidines 8 a–8 g in high chemical yields and with moderate diastereoselectivities from the ß‐monosubstituted substrates. The analogous α‐substituted GABA derivatives 11 a–11 c were also applied as potential substrates for memory of chirality effects. The reaction quantum yields of the photodecarboxylation reactions for the parent GABA derivative 13 and for the new substrates 7 h and 11 a were determined by the quantum yield determination system (QYDS) and showed a remarkable concentration dependency indicating aggregation at higher substrate concentrations. Inhibition studies on the atherogenic human serine hydrolase cholesterol esterase showed derivatives 8 a and 8 d to exhibit a hyperbolic mode of inhibition with moderate IC50 values of about 60–80 μM.
KW  - Fotochemie
KW  - Heterocycles
KW  - Photochemistry
KW  - Radicals
KW  - Decarboxylation
KW  - Quantum Yields
Y1  - 2024
UN  - https://nbn-resolving.org/urn:nbn:de:hbz:832-epub4-27906
SN  - 2367-0932
SS  - 2367-0932
U6  - https://doi.org/10.1002/cptc.202400033
DO  - https://doi.org/10.1002/cptc.202400033
VL  - 8
IS  - 8
SP  - 6
S1  - 6
ER  -