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

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 he...

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Bibliographic Details
Published in:	Journal of organic chemistry Vol. 88; no. 13; pp. 9469 - 9474
Main Authors:	Skrzypczak, Natalia, Pyta, Krystian, Bohusz, Wiktor, Leśniewska, Aleksandra, Gdaniec, Maria, Ruszkowski, Piotr, Schilf, Wojciech, Bartl, Franz, Przybylski, Piotr
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 07-07-2023
Subjects:	Benzoquinones Benzoxazoles - pharmacology Lactams, Macrocyclic - pharmacology Rifabutin
Online Access:	Get full text
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Summary:	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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.3c00493