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Synthesis and structure of dihydroberberine nitroaryl derivatives – potential ligands for G-quadruplexes

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Chemistry of Heterocyclic Compounds Aims and scope

A method was developed for the synthesis of dihydroberberine nitroaryl derivatives on the basis of dihydroberberine reactions with aromatic electrophiles (picryl chloride, 4-chloro-7-nitrobenzofurazan, 4-chloro-5,7-dinitrobenzofurazan, and 7-chloro-4,6-dinitrobenzofuroxan). The obtained 13-substituted dihydroberberine derivatives represent structures with significant intramolecular charge transfer and, according to the results of molecular docking analysis, can effectively bind with G-quadruplexes of telomeric DNA fragments.

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Acknowledgements

This study was supported by a grant from the Russian Science Foundation (project 14-13-00103).

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Authors and Affiliations

  1. Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    Oleg N. Burov, Sergey V. Kurbatov, Mikhail E. Kletskii, Alexander D. Zagrebaev & Igor E. Mikhailov

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  1. Oleg N. Burov
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  2. Sergey V. Kurbatov
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  3. Mikhail E. Kletskii
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  4. Alexander D. Zagrebaev
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  5. Igor E. Mikhailov
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Correspondence to Oleg N. Burov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(3), 335–340

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Burov, O.N., Kurbatov, S.V., Kletskii, M.E. et al. Synthesis and structure of dihydroberberine nitroaryl derivatives – potential ligands for G-quadruplexes. Chem Heterocycl Comp 53, 335–340 (2017). https://doi.org/10.1007/s10593-017-2055-3

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  • DOI: https://doi.org/10.1007/s10593-017-2055-3

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