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Bicyclic nucleoside analogues: synthesis of thiazolopyrimidine-based nucleosides a copper-catalysed tandem reaction of 5-iodocytidine with isothiocyanates.
Org Biomol Chem
January 2025
Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology (CSIR-NIIST), Thiruvananthapuram 695019, India.
We have devised a copper-catalysed tandem annulation reaction to generate a new class of bicyclic nucleoside analogues (BCNAs), namely, amino-substituted thiazolopyrimidine ribonucleosides. The reaction between triacetyl-5-iodo-cytidine and an appropriate organic isothiocyanate in the presence of a Cu salt and ligand resulted in the formation of an amino-substituted thiazolopyrimidine moiety. This reaction was found to be compatible with a range of aliphatic and aromatic isothiocyanates, affording the corresponding products in moderate to good yields.
View Article and Find Full Text PDFLignin-Based Mucus-Mimicking Antiviral Hydrogels with Enzyme Stability and Tunable Porosity.
ACS Appl Mater Interfaces
January 2025
Institute for Chemistry and Biochemistry, Freie Universität Berlin, Berlin 14195, Germany.
Mucus is a complex hydrogel that acts as a defensive and protective barrier in various parts of the human body. The rise in the level of viral infections has underscored the importance of advancing research into mucus-mimicking hydrogels for the efficient design of antiviral agents. Herein, we demonstrate the gram-scale synthesis of biocompatible, lignin-based virus-binding inhibitors that reduce waste and ensure long-term availability.
View Article and Find Full Text PDFHigh-yielding total synthesis of embelin, rapanone, and irisoquin A, D, F.
Org Biomol Chem
January 2025
Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046, India.
Simple and sustainable three- and four-step sequences of di-OH-protection/mono-OMe-deprotection/OrgRC and di-OH-protection/mono-OMe-deprotection/OrgRC/OMe-deprotection protocols were developed to construct biologically active natural products of irisoquin, irisoquin A, irisoquin D, irisoquin F, sorgoleone-364, embelin, rapanone, 5--methylembelin, 5--methylrapanone and their analogues from the commercially available 2,5-dihydroxy-1,4-benzoquinone, aliphatic aldehydes and Hantzsch ester (1,4-DHP) in very good to excellent yields by using organocatalytic reductive coupling (OrgRC) as key reaction. Many of these natural compounds exhibited a broad spectrum of biological activities including antioxidant, anti-inflammatory, anticonvulsant, anxiolytic, analgesic, anthelmintic, antitumor, antibacterial, and antifertility properties. At the same time, simple and readily available 2,5-dihydroxy-1,4-benzoquinone was transformed into a functionally rich library of 2,5-dihydroxy-3,6-dialkyl-1,4-benzoquinones in very good yields by using sequential OrgRC followed by deprotection reactions and resulting natural/unnatural products would be excellent targets for investigation to show their biological activities compared to known natural products.
View Article and Find Full Text PDFBromide-promoted cascade annulation of isocyanobiaryls with aldehydes through photoredox catalysis.
Org Biomol Chem
January 2025
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions.
View Article and Find Full Text PDFSynthesis and Polymerization of Thiophene-Bearing 2-Oxazolines and 2-Oxazines.
Macromol Rapid Commun
January 2025
Department of Bioengineering, Imperial College London, South Kensington, London, SW7 2AZ, UK.
Intrinsically conductive polymers have garnered a great deal of attention for use in medical and bioelectronic applications. Despite this, challenges associated with the mechanical stability, processability, and fabrication of conducting polymers have limited their utility. To circumvent these limitations, thiophene substituted 2-oxazolines (2Ox) and 2-oxazines (2Ozi) are introduced, which can be polymerized to form a thermally stable and potentially melt-processable polymers as precursors for conductive polymers.
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