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SYNTHESIS AND STRUCTURE OF DIHYDROBERBERINE NITROARYL DERIVATIVES – POTENTIAL LIGANDS FOR G-QUADRUPLEXES

Олег Н. Буров, Сергей В. Курбатов, Михаил Е. Клецкий, Александр Д. Загребаев, Игорь Е. Михайлов
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Abstract


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-dinitro-benzofuroxan). 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 Gquadruplexes of telomeric DNA fragments.

 

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


Keywords


берберин; дигидроберберин; 4,6-динитробензофуразан; 4,6-динитробензофуроксан; G-квадруплекс; молекулярный докинг; нуклеофильное ароматическое замещение; DFT-расчеты

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