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Simple methods of modification of daunorubicin on the daunosamine nitrogen atom

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Abstract

Modification of daunorubicin on its NH2 moiety is a well-established synthetic approach to obtain novel derivatives of this compound. Moreover, the daunosamine moiety of this antibiotic is considered to be the most sensitive part of a molecule in terms of biological response to chemical transformations. Using simple and effective synthetic techniques, namely, alkylation under phase-transfer catalysis and an amine addition across an activated multiple bond, a series of daunorubicin derivatives retaining the amine functionality have been obtained, which could also be used as potential precursors for further transformations.

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Acknowledgements

This work was supported by RFBR (№ 18-03-00073) and the scholarship of the President of the Russian Federation for young scientists and postgraduates (Competition «SP-2019», No SP-2717.2019.4). NMR studies, spectral characterization, and elemental analysis were performed with the financial support from Ministry of Science and Higher Education of the Russian Federation using the equipment of Center for molecular composition studies of INEOS RAS.

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Authors and Affiliations

  1. A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS), Moscow, 119991, Russia

    Valery K. Brel, Aleksandra A. Moiseeva, Oleg I. Artyushin, Lada V. Anikina & Zinaida S. Klemenkova

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  1. Valery K. Brel
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  2. Aleksandra A. Moiseeva
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  3. Oleg I. Artyushin
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  4. Lada V. Anikina
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  5. Zinaida S. Klemenkova
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Correspondence to Valery K. Brel.

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Brel, V.K., Moiseeva, A.A., Artyushin, O.I. et al. Simple methods of modification of daunorubicin on the daunosamine nitrogen atom. Med Chem Res 30, 564–573 (2021). https://doi.org/10.1007/s00044-020-02664-8

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