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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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
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author Skrzypczak, Natalia
Pyta, Krystian
Bohusz, Wiktor
Leśniewska, Aleksandra
Gdaniec, Maria
Ruszkowski, Piotr
Schilf, Wojciech
Bartl, Franz
Przybylski, Piotr
author_facet Skrzypczak, Natalia
Pyta, Krystian
Bohusz, Wiktor
Leśniewska, Aleksandra
Gdaniec, Maria
Ruszkowski, Piotr
Schilf, Wojciech
Bartl, Franz
Przybylski, Piotr
author_sort Skrzypczak, Natalia
collection PubMed
description [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.
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spelling pubmed-103370342023-07-13 Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity Skrzypczak, Natalia Pyta, Krystian Bohusz, Wiktor Leśniewska, Aleksandra Gdaniec, Maria Ruszkowski, Piotr Schilf, Wojciech Bartl, Franz Przybylski, Piotr J Org Chem [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. American Chemical Society 2023-06-05 /pmc/articles/PMC10337034/ /pubmed/37276434 http://dx.doi.org/10.1021/acs.joc.3c00493 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Skrzypczak, Natalia
Pyta, Krystian
Bohusz, Wiktor
Leśniewska, Aleksandra
Gdaniec, Maria
Ruszkowski, Piotr
Schilf, Wojciech
Bartl, Franz
Przybylski, Piotr
Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title_full Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title_fullStr Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title_full_unstemmed Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title_short Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity
title_sort cascade transformation of the ansamycin benzoquinone core into benzoxazole influencing anticancer activity and selectivity
url 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
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