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Tunable and Photoactivatable Mimics of Calicheamicin γ for DNA Cleavage.
J Am Chem Soc
September 2024
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
Calicheamicin γ and related natural products are renowned for their potency in DNA cleavage, serving as the warheads in commercial ADCs used for treating leukemia. Their mechanism of action involves the formation of aryl radicals, which abstract hydrogen atoms from nucleic acids. However, the complex strained enediyne structure of calicheamicin γ presents significant challenges in synthesis, resulting in high production costs and limited structural and activity modularity for tuning the therapeutic window.
View Article and Find Full Text PDFAgNOx as Nitrogen Source for [1+1+3] Cycloaddition of Isocyanides with Isocyanates: Selective Synthesis of 1,2,4-Triazoles.
Org Lett
August 2024
School of Environmental and Chemical Engineering, Wuyi University, Jiangmen 529020, China.
A novel [1+1+3] annulation of AgNOx, isocyanides, and isocyanates for the selective synthesis of 1,2,4-triazoles is presented herein. In this transformation, AgNOx and isocyanates are used as nitrogen sources instead of the traditional hydrazine or diazonium reagents. This process also involves N-O/C-H/C═N bond cleavage and the construction of new N-N/C-N bonds with a good substrate scope and functional group tolerance.
View Article and Find Full Text PDFPhotosensitized Activation of Diazonium Derivatives for C-B Bond Formation.
Chem Catal
February 2023
Université catholique de Louvain (UCLouvain), Institut de la Matière Condensée et des Nanosciences (IMCN), Molecular Chemistry, Materials and Catalysis (MOST), Place Louis Pasteur 1, bte L4.01.02, 1348 Louvain-la-Neuve, Belgium.
Aryl diazonium salts are ubiquitous building blocks in chemistry, as they are useful radical precursors in organic synthesis as well as for the functionalization of solid materials. They can be reduced electrochemically or through a photo-induced electron transfer reaction. Here we provide a detailed picture of the ground and excited-state reactivity of a series of 9 rare and earth abundant photosensitizers with 13 aryl diazonium salts, which also included 3 macrocyclic calix[4]arene tetradiazonium salts.
View Article and Find Full Text PDFSynthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes.
Beilstein J Org Chem
November 2021
Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology, Campus North, Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany.
We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3-pyrazolo[3,4-][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introduction of two side chains allowed a variation of the pyrazolo[3,4-][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly.
View Article and Find Full Text PDFPhotocatalytic intermolecular carboarylation of alkenes by selective C-O bond cleavage of diarylethers.
Chem Commun (Camb)
September 2021
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China.
Disclosed herein is a novel radical-mediated intermolecular carboarylation of alkenes by cleaving inert C-O bonds. The strategically designed arylbenzothiazolylether diazonium salts are harnessed as dual-function reagents. A vast array of alkenes are proven to be suitable substrates.
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