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Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity

[Image: see text] The metal-free cascade transformation of geldanamycin benzoquinone core is proposed at relatively mild conditions. This approach yields new benzoxazole ansamycin antibiotics and enables their functionalization in an atom-economic manner, irrespective of the type of amine used. The...

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Detalles Bibliográficos
Autores principales: Skrzypczak, Natalia, Pyta, Krystian, Bohusz, Wiktor, Leśniewska, Aleksandra, Gdaniec, Maria, Ruszkowski, Piotr, Schilf, Wojciech, Bartl, Franz, Przybylski, Piotr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10337034/
https://www.ncbi.nlm.nih.gov/pubmed/37276434
http://dx.doi.org/10.1021/acs.joc.3c00493
Descripción
Sumario:[Image: see text] The metal-free cascade transformation of geldanamycin benzoquinone core is proposed at relatively mild conditions. This approach yields new benzoxazole ansamycin antibiotics and enables their functionalization in an atom-economic manner, irrespective of the type of amine used. The analysis of the heterocyclization course reveals the dependence of its rate on the nature of the para-substituent within the benzylamine moiety (EDG/EWG) and the strength of the base. The reduction of the ansamycin core enables an increase in anticancer potency and selectivity.