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The Synthesis and Investigation of New Electroneutral Berberine Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

The possibility of obtaining electroneutral 8-substituted berberines was demonstrated experimentally as well as by DFT/B3LYP and ab initio MP2/HF quantum-chemical calculations with the 6-311+G(d,p) basis set. In alkaline media, it is possible to substitute the C-8 position of berberine with such C-nucleophiles as methyl ketones, acetic acid esters, nitriles, geminal di- and trihaloalkanes. This process proceeds stepwise. First, berberine is attacked by a hydroxide anion to form a covalently bonded 8-hydroxyberberine, then 8-hydroxyberberine reacts with a nucleophile in the nonionized (molecular) form.

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Authors and Affiliations

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

    Alexander D. Zagrebaev, Oleg N. Burov, Mikhail Е. Kletskii, Anton V. Lisovin, Sergey V. Kurbatov & Oleg D. Demekhin

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  1. Alexander D. Zagrebaev
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  2. Oleg N. Burov
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  3. Mikhail Е. Kletskii
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  4. Anton V. Lisovin
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  5. Sergey V. Kurbatov
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  6. Oleg D. Demekhin
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Correspondence to Oleg N. Burov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(1), 45–57

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Zagrebaev, A.D., Burov, O.N., Kletskii, M.Е. et al. The Synthesis and Investigation of New Electroneutral Berberine Derivatives. Chem Heterocycl Comp 58, 45–57 (2022). https://doi.org/10.1007/s10593-022-03055-0

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