Invited for the cover of this issue is the group of Frederic W. Patureau at the RWTH Aachen University. The image depicts atropoisomerism, in particular through the helix-shaped vines in the forefront focus. This metaphorically illustrates the importance of atroposelectivity in biologically active molecules, such as in the 5-hydroxyindoles that were accessed through the first enantioselective Nenitzescu indole synthesis. Read the full text of the article at 10.1002/chem.202300279.
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Repurposing anti-inflammatory drugs for fighting planktonic and biofilm growth. New carbazole derivatives based on the NSAID carprofen: synthesis, and bioevaluation.
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Department of Pharmaceutical Chemistry, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy, Bucharest, Romania.
Introduction: One of the promising leads for the rapid discovery of alternative antimicrobial agents is to repurpose other drugs, such as nonsteroidal anti-inflammatory agents (NSAIDs) for fighting bacterial infections and antimicrobial resistance.
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Atroposelective Nenitzescu Indole Synthesis.
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May 2023
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Invited for the cover of this issue is the group of Frederic W. Patureau at the RWTH Aachen University. The image depicts atropoisomerism, in particular through the helix-shaped vines in the forefront focus.
View Article and Find Full Text PDFAtroposelective Nenitzescu Indole Synthesis.
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May 2023
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
In the past decade, compounds bearing a stereogenic C-N axis have gained significant attention in fields ranging from ligand to drug design. Yet, the atroposelective synthesis of these molecules remains a considerable challenge. In contrast to recent methods using more advanced chiral catalysts, a very simply accessed Jacobsen-type chromium(III)-salen complex was used here as a chiral enantiopure Lewis acid catalyst for a highly atroposelective Nenitzescu indole synthesis.
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Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira Street 19, 620002 Ekaterinburg, Russia.
This paper reports the synthesis of four types of annulated pyranoindole congeners: pyrano[3,2-]indole, pyrano[2,3-]indole, pyrano[2,3-]indole, and pyrano[2,3-]indole and photophysical studies in this series. The synthesis of pyrano[3,2-], [2,3-], and [2,3-]indoles involve a tandem of Bischler-Möhlau reaction of 3-aminophenol with benzoin to form 6-hydroxy- or 4-hydroxyindole followed by Pechmann condensation of these hydroxyindoles with β-ketoesters. Pyrano[2,3-]indoles were synthesized through the Nenitzescu reaction of -benzoquinone and ethyl aminocrotonates and subsequent Pechmann condensation of the obtained 5-hydroxyindole derivatives.
View Article and Find Full Text PDFIn Silico and Experimental Investigation of the Biological Potential of Some Recently Developed Carprofen Derivatives.
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Department of Anatomy, Animal Physiology, and Biophysics, Faculty of Biology, University of Bucharest, 36-46 M. Kogălniceanu Boulevard, 050107 Bucharest, Romania.
The efficient regioselective bromination and iodination of the nonsteroidal anti-inflammatory drug (NSAID) carprofen were achieved by using bromine and iodine monochloride in glacial acetic acid. The novel halogenated carprofen derivatives were functionalized at the carboxylic group by esterification. The regioselectivity of the halogenation reaction was evidenced by NMR spectroscopy and confirmed by X-ray analysis.
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