A new reaction swaps an oxygen for a nitrogen in structurally complex molecules.
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One-Step Realization of Skeleton Editing, -Dinitromethyl Functionalization, and Zwitterionization in a Laser-Sensitive 1,3,4-Oxadiazole Energetic Molecule.
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School of Astronautics, Northwestern Polytechnical University, Xi'an, Shaanxi 710065, China.
The single-atom skeletal editing technology is an efficient method for constructing molecular skeletons, which has broad coverage in synthetic chemistry. However, its potential in the preparation of energetic heterocyclic molecules is grossly underexplored. In this work, an unexpected one-step reaction for the synthesis of novel energetic molecules was discovered which combines single-atom skeletal editing, -dinitromethyl functionalization, and zwitterionization in one step.
View Article and Find Full Text PDFHarnessing the Sulfur-for-Oxygen Shift: A Magic Bullet for Dynamic Photophysical and Anticancer Activities of Indole-Barbituric Acid Construct.
ChemMedChem
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IIT Roorkee: Indian Institute of Technology Roorkee, Chemistry, Department of Chemistry, 247667, Roorkee, INDIA.
The development of small molecule-based drugs emerged as a cornerstone of modern drug discovery. Structural activity relationship (SAR) studies in medicinal chemistry are crucial for lead optimization, where a subtle change in the substituent can significantly alter its binding affinity with the biological target. Herein, a highly efficient single-atom substitution (SAS) approach has been developed, where sulfur for oxygen strategy is utilized as a powerful molecular editing technique to identify N-vinyl Indole-thiobarbituric acid (6a) as a novel small molecule-based scaffold with tunable photophysical and antiproliferative activities.
View Article and Find Full Text PDFA Formal 1,2-Stevens Rearrangement of Thioester Ylides as a Single-Atom Molecular Editing Tool.
Org Lett
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University of Belgrade, Faculty of Chemistry, Studentski trg 16, P.O. Box 51, 11158 Belgrade 118, Serbia.
A rhodium-catalyzed reaction of thioesters with diazo reagents was recognized as a powerful and unprecedented tool for single-atom molecular editing by the insertion of a single carbon atom into the C(O)─S thioester bond, thereby leading to various α-thioketones possessing a quaternary carbon atom. A selective and precise defunctionalization of the polyfunctionalized products further demonstrated the synthetic utility of the reaction for the synthesis of more common structural classes of compounds.
View Article and Find Full Text PDFTriftosylhydrazone in Single-Atom Skeletal Editing.
Acc Chem Res
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Department of Chemistry, Northeast Normal University, Changchun 130024, China.
ConspectusIn the past decade, single-atom skeletal editing, which involves the precise insertion, deletion, or exchange of single atoms in the core skeleton of a molecule, has emerged as a promising synthetic strategy for the rapid construction or diversification of complex molecules without laborious synthetic processes. Among them, carbene-initiated skeletal editing is particularly appealing due to the ready availability and diverse reactivities of carbene species. The initial endeavors to modify the core skeleton of heteroarenes through carbon-atom insertion could date back to 1881, when Ciamician and Denstedt described the conversion of pyrroles to pyridines by trapping haloform-derived free carbene.
View Article and Find Full Text PDFIdentification of bioactive compounds with popular single-atom modifications: Comprehensive analysis and implications for compound design.
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Department of Pharmacy, The Affiliated Hospital of Yangzhou University, Yangzhou University, Yangzhou, 225000, PR China; Science for Life Laboratory, Department of Cell and Molecular Biology, Uppsala University, BMC, Box 596, SE-751 24, Uppsala, Sweden; Centre for Cancer Drug Discovery, Division of Cancer Therapeutics, The Institute of Cancer Research, London, UK. Electronic address:
The extensive bioactivity data available in public databases, such as ChEMBL, has facilitated in-depth structure-activity relationship (SAR) analysis, which are essential for understanding the impact of molecular modifications on biological activity in a comprehensive manner. A central strategy in SAR analysis is the assessment of molecular similarity. Several approaches preferred by medicinal chemists have been developed to efficiently capture structurally related compounds on a large scale.
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