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Protecting‐Group‐Free One‐Step Palladium‐Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells

Protecting‐Group‐Free One‐Step Palladium‐Catalyzed Coupling on C25 of Cucurbitacin B Expands... The natural product cucurbitacin B has been widely studied because of its multiple biological activities, especially its potent antitumor effects. However, modifications of cucurbitacin B are mainly focused on the C2 and C16 site, studies on the C25 acetoxy group are still limited. We successfully developed a palladium‐catalyzed allylic coupling of cucurbitacin B with boronic acids, providing a one‐step approach to expand the chemical diversity of the C25 position. Our method was protecting‐group‐free, showing a good functional group tolerance and a wide substrate scope under mild reaction conditions. A library of 29 derivatives was prepared, compounds 2q and 2u showed higher cytotoxicity against A549 cells than cucurbitacin B, compounds 2n and 2o maintained potency, and the introduced hydroxyl and amino groups could be further derived. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Protecting‐Group‐Free One‐Step Palladium‐Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells

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Publisher
Wiley
Copyright
© 2022 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH
eISSN
1614-7065
DOI
10.1002/cjoc.202200106
Publisher site
See Article on Publisher Site

Abstract

The natural product cucurbitacin B has been widely studied because of its multiple biological activities, especially its potent antitumor effects. However, modifications of cucurbitacin B are mainly focused on the C2 and C16 site, studies on the C25 acetoxy group are still limited. We successfully developed a palladium‐catalyzed allylic coupling of cucurbitacin B with boronic acids, providing a one‐step approach to expand the chemical diversity of the C25 position. Our method was protecting‐group‐free, showing a good functional group tolerance and a wide substrate scope under mild reaction conditions. A library of 29 derivatives was prepared, compounds 2q and 2u showed higher cytotoxicity against A549 cells than cucurbitacin B, compounds 2n and 2o maintained potency, and the introduced hydroxyl and amino groups could be further derived.

Journal

Chinese Journal of ChemistryWiley

Published: Jul 15, 2022

Keywords: Natural products; Cucurbitacin B; Palladium‐catalyzed couplingl Divergent synthesis; Structure‐activity relationships

References