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New Insights into the Modifications and Bioactivities of Indole-3-Carboxaldehyde and its Derivatives as a Potential Scaffold for Drug Design: A Mini-Review.
Mini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFMembrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes.
ACS Appl Mater Interfaces
January 2025
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Miklukho-Maklaya 16/10, 117997 Moscow, Russia.
Enveloped viruses, such as flaviviruses and coronaviruses, are pathogens of significant medical concern that cause severe infections in humans. Some photosensitizers are known to possess virucidal activity against enveloped viruses, targeting their lipid bilayer. Here we report a series of halogenated difluoroboron-dipyrromethene (BODIPYs) photosensitizers with strong virus-inactivating activity.
View Article and Find Full Text PDFAssembly of Pyrenes through a Quadruple Photochemical Cascade: Blocking Groups Allow Diversion from the Double Mallory Path to Photocyclization at the Bay Region.
J Am Chem Soc
January 2025
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306, United States.
We present a six-step cascade that converts 1,3-distyrylbenzenes (-stilbenes) into nonsymmetric pyrenes in 40-60% yields. This sequence merges photochemical steps, ,-alkene isomerization, a 6π photochemical electrocyclization (Mallory photocyclization); the new bay region cyclization, with two radical iodine-mediated aromatization steps; and an optional aryl migration. This work illustrates how the inherent challenges of engineering excited state reactivity can be addressed by logical design.
View Article and Find Full Text PDFA cross-shaped organic framework: a multi-functional template arranging chromophores.
Org Chem Front
December 2024
Department of Chemistry, University of Basel St Johanns-Ring 19 Basel 4056 Switzerland https://www.chemie1.unibas.ch/Bmayor/.
This work explores the use of a cross-shaped organic framework that is used as a template for the investigation of multi-functionalized chromophores. We report the design and synthesis of a universal cross-shaped building block bearing two bromines and two iodines on its peripheral positions. The template can be synthesized on a gram scale in a five-step reaction comprising an oxidative homo-coupling macro-cyclization.
View Article and Find Full Text PDFRevealing the Role of Electronic Effect to Modulate the Photophysics and Z-Scan Responses of -Locked GFP Chromophores.
J Phys Chem B
January 2025
Department of Chemistry and Chemical Biology, Indian Institute of Technology (Indian School of Mines) Dhanbad, Dhanbad826004, Jharkhand, India.
Three novel core green fluorescent protein (GFP) chromophore analogues, based on a doubly locked conformation and variable electronic effects by replacing one hydrogen with bromine, iodine, and methyl, respectively, have been synthesized to modulate the push-pull effect. These chromophores exhibited intramolecular H-bonding, as evidenced by single-crystal X-ray and H NMR studies. The fluorescence quantum yields (ϕ) of all of the chromophores were found to be more than an order of magnitude higher (∼0.
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