A variety of novel imidazolidinone-based organocatalysts with bulky substituents were synthesized under mild reaction conditions starting from easily accessible substrates. Different natural and unnatural amino acid methyl amides were cyclized with aromatic carbaldehydes to yield two diastereomeric MacMillan-type catalysts. Special emphasis was put on bulky residues such as mesityl and pyrene moieties.
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http://dx.doi.org/10.3762/bjoc.13.254 | DOI Listing |
J Org Chem
December 2022
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
We report a general method for the desymmetrization of 6,13-pentacenequinone to access ethynylated pentacene ketones, namely, 13-hydroxy-13-(ethynylated)pentacene-6(13)-ones. These pentacene ketones ("pentacenones") serve as divergent intermediates to unsymmetrically 6,13-disubstituted pentacenes, commonly used for studying singlet fission processes and charge transport phenomena in organic field effect transistors. We report a synthetic method to access pentacenones, which utilizes a precipitation/crystallization from the crude mixture to enable facile purification on a multigram scale.
View Article and Find Full Text PDFJ Am Chem Soc
May 2022
Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, F-35000 Rennes, France.
We report on the synthesis and self-assembly of 2,15- and 4,13-disubstituted carbo[6]helicenes and bearing 3,4,5-tridodecyloxybenzamide groups. The self-assembly of these [6]helicenes is strongly influenced by the substitution pattern in the helicene core that affects the mutual orientation of the monomeric units in the aggregated form. Thus, the 2,15-substituted derivative undergoes an isodesmic supramolecular polymerization forming globular nanoparticles that maintain circularly polarized light (CPL) with values as high as 2 × 10.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2022
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37073, Göttingen, Germany.
A highly enantioselective synthesis of 5,13-disubstituted dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophenes is reported. Key for the successful assembly of these helical architectures is the last two successive Au-catalyzed intramolecular alkyne hydroarylation events. Specifically, the second cyclization is the enantiodetermining step of the whole process and provides the desired helicenes with excellent ee values when a TADDOL-derived 1,2,3-(triazolium)phosphonite moiety (TADDOL: α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol) is employed as an ancillary ligand.
View Article and Find Full Text PDFBioorg Med Chem Lett
January 2020
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development & Shanghai Key Laboratory of Green Chemistry and Chemical Processes, SCME, East China Normal University, Shanghai 200062, China. Electronic address:
Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC value of 0.
View Article and Find Full Text PDFEur J Med Chem
February 2017
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, SCME, East China Normal University, Shanghai 200062, China. Electronic address:
A series of novel 9, 13-disubstituted berberine derivatives have been synthesized and evaluated for the antibacterial activities against Staphylococcus aureus, including Newman strain and multidrug-resistant strains (NRS-1, NRS-70, NRS-100, NRS-108, and NRS-271). Compound 20 shows the most potent activity against the growth of Newman strain, with a MIC value of 0.78 μg/mL, which is comparable with the positive control vancomycin.
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