@article{SchulzeZimmerNeud{\"o}rfletal.2024,
  author    = {Schulze, Wolfram and Zimmer, Anne and Neud{\"o}rfl, J{\"o}rg-Martin and Dato, Florian M. and Sommerfeld, Paul and Pietsch, Markus and Derondeau, Henrieta and Gaida, Florian and Riedle, Eberhard and Griesbeck, Axel G.},
  title     = {Photodecarboxylative Ring Annulation of α- and β-Functionalized Phthaloyl-GABA Derivatives: Bioactive Pyrroloisoindolinones with High Quantum Efficiency},
  journal   = {ChemPhotoChem},
  volume    = {8},
  number    = {8},
  issn      = {2367-0932},
  doi       = {10.1002/cptc.202400033},
  institution = {Angewandte Naturwissenschaften (F11)},
  pages     = {6},
  year      = {2024},
  abstract  = {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.},
  subject      = {Fotochemie},
  language  = {en}
}