Functionalization of bioactive substrates with a F₅SCH = CH moiety

ABSTRACT

A convenient approach to modify bioactive substrates such as daunorubicin, cytisine, and camphecene with a pentafluorosulfanylvinyl moiety have been suggested. F₅S-CH = CH derivatives of daunorubicin were obtained by acylation with reactive 4-nitrophenyl-4-(pentafluoro-λ⁶-sulfanyl)alkenyl carbonates, while the corresponding conjugates of anthracycline antibiotic daunorubicin, alkaloid cytisine and camphecene were synthesized using a click chemistry procedure.

GRAPHICAL ABSTRACT

KEYWORDS:

• Fluorosulfanylvinyl derivatives
• daunorubicin
• cytisine
• camphecene
• click reactions

Acknowledgements

This work was supported by RFBR (No 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, elemental analysiswere 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.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by RFBR [grant number 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, elemental analysiswere 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.