1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (−)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing

Shybanov, D.E.; Kukushkin, M.E.; Grishin, Y.K.; Roznyatovsky, V.A.; Tafeenko, V.A.; Qoura, L.A.; Pokrovsky, V.S.; Yarovaya, O.I.; Belyaevskaya, S.V.; Volobueva, A.S.; Esaulkova, I.L.; Zarubaev, V.V.; Beloglazkina, E.K.

Авторы: Shybanov Dmitry E., Kukushkin Maxim E., Grishin Yuri K., Roznyatovsky Vitaly A., Tafeenko Viktor A., Qoura Louay Abo, Pokrovsky Vadim S., Yarovaya Olga I., Belyaevskaya Svetlana V., Volobueva Alexandrina S., Esaulkova Iana L., Zarubaev Vladimir V., Beloglazkina Elena K.
Журнал: International Journal of Molecular Sciences
Том: 25
Номер: 21
Год издания: 2024
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 11435
DOI: 10.3390/ijms252111435
Аннотация: The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrilimines to caryophyllene was demonstrated. As a result of these reactions, pharmacophore fragments of isoxazoline and pyrazoline are introduced into the structure of caryophyllene, which leads to an increase in the conformational rigidity of the molecule. A complete stereochemical assignment of 1,3-dipolar cycloaddition adducts to caryophyllene was carried out. The study of antiviral and cytotoxic activity for some heterocyclic derivatives synthesized in this work revealed relatively high biological activity of previously little-studied cycloaddition adducts at the exocyclic C=CH2 bond of caryophyllene. The effect of substituents in the synthesized heterocycles on biological activity was demonstrated. Compounds with a good inhibitory effect on the H1N1 influenza virus were revealed. The activity of the compound was demonstrated up to 6 h post infection, and this could be due to slight inhibiting activity against viral neuraminidase, necessary at the stage of progeny virion budding.
Добавил в систему: Белоглазкина Елена Кимовна

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1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (−)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testingстатья

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