Dill M, Attia D, Mokhir A (2025)
Publication Type: Journal article
Publication year: 2025
Book Volume: 2025
Article Number: 202512322
Journal Issue: 5
DOI: 10.24820/ark.5550190.p012.322
Prodrugs can achieve targeting of cancer cells. Therefore, their application can improve the therapy of cancer diseases. The best aminoferrocene-based prodrug developed in the group of Mokhir is 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl (3-(piperidin-1-ylmethyl)benzyl) (ferrocenyl)carbamate, NCure2. It targets lysosomes of cancer cells, where it is activated by H2O2. Due to the presence of basic (amine) and Lewis acidic (boronic acid pinacol ester) moieties in NCure2, the previous synthesis is low yielding and purification is laborious. In this work we report on a significantly improved synthetic protocol for preparation of HCl salt of NCure2 by introducing the boronic acid moiety in the last synthetic step via Miyaura borylation conditions that allows the facile purification of the final product by its precipitation. This new approach makes NCure2·HCl more synthetically accessible that will facilitate its further pre-clinical and clinical studies.
APA:
Dill, M., Attia, D., & Mokhir, A. (2025). Synthesis of a lysosome-targeting aminoferrocene-based prodrug NCure2. Arkivoc, 2025(5). https://doi.org/10.24820/ark.5550190.p012.322
MLA:
Dill, Maximilian, Dina Attia, and Andriy Mokhir. "Synthesis of a lysosome-targeting aminoferrocene-based prodrug NCure2." Arkivoc 2025.5 (2025).
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