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

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Authors
Skrzypczak, Natalia
Pyta, Krystian
Bohusz, Wiktor
Leśniewska, Aleksandra
Gdaniec, Maria
Ruszkowski, Piotr
Schilf, Wojciech
Bartl, Franz
Przybylski, Piotr
Date
2023
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
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.
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Citation
J. Org. Chem. 2023, 88, 9469−9474 ; https://doi.org/10.1021/acs.joc.3c00493
URI
https://open.icm.edu.pl/handle/123456789/23524
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