For the first time, amides and ureas based on both 5-nitroisoquinoline and 5-nitrosoisoquinoline were obtained by direct nucleophilic substitution of hydrogen in the 5-nitroisoquinoline molecule. In the case of urea and monosubstituted ureas, only 5-nitrosoisoquinoline-6-amine is formed under anhydrous conditions.
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http://dx.doi.org/10.3390/molecules27227862 | DOI Listing |
Molecules
November 2024
Bioorganic & Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry & Biomedical Sciences, Linnaeus University, SE-39182 Kalmar, Sweden.
Unsymmetrical urea derivatives are essential structural motifs in a wide array of biologically significant compounds. Despite the well-established methods for synthesizing symmetrical ureas, efficient strategies for the synthesis of unsymmetrical urea derivatives remain limited. In this study, we present a novel approach for the synthesis of unsymmetrical urea derivatives through the coupling of amides and amines.
View Article and Find Full Text PDFNat Commun
November 2024
Department of Physiology and Pathophysiology, School of Basic Medical Sciences, State Key Laboratory of Vascular Homeostasis and Remodeling, Beijing Key Laboratory of Cardiovascular Receptors Research, Peking University, Beijing, China.
Angew Chem Int Ed Engl
November 2024
Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie-Curie Pvt, Ottawa, ON, K1N 6N5, Canada.
Linchpin reagents are building blocks that can be chemoselectively functionalized to afford products with a common, useful functional group. In this work, we describe the development and validation of the first amide linchpin reagent and demonstrate its use as a doubly electrophilic building block for the synthesis of a variety of amides, including challenging classes. The linchpin reagent was first functionalized via rhodium-catalyzed electrophilic amination.
View Article and Find Full Text PDFJ Med Chem
November 2024
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Egyptian Russian University, Badr City, Cairo 11829, Egypt.
Hypoxia in tumors contributes to chemotherapy resistance, worsened by acidosis driven by carbonic anhydrases (CA IX and XII). Targeting these enzymes can mitigate acidosis, thus enhancing tumor sensitivity to cytotoxic drugs. Herein, novel 4-(pyrazolyl)benzenesulfonamide ureas () were developed and evaluated for their inhibitory activity against CA IX and XII.
View Article and Find Full Text PDFScience
November 2024
Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
Unsymmetrical ureas are commonly found in pharmaceuticals and bioactive compounds. However, devising strategies to introduce two distinct amines selectively in the construction of unsymmetrical ureas remains a challenge. In this work, we use a synchronous recognition strategy that takes advantage of radical and nucleophilic activation to discriminate between secondary and primary amines.
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