[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones

Kuznetsova, J.V.; Tkachenko, V.T.; Petrovskaya, L.M.; Filkina, M.E.; Shybanov, D.E.; Grishin, Y.K.; Roznyatovsky, V.A.; Tafeenko, V.A.; Pestretsova, A.S.; Yakovleva, V.A.; Pokrovsky, V.S.; Kukushkin, M.E.; Beloglazkina, E.K.

Статья опубликована в высокорейтинговом журнале

Информация о цитировании статьи получена из Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 1 мая 2024 г.

Авторы: Kuznetsova Juliana V., Tkachenko Varvara T., Petrovskaya Lada M., Filkina Maria E., Shybanov Dmitry E., Grishin Yuri K., Roznyatovsky Vitaly A., Tafeenko Viktor A., Pestretsova Anna S., Yakovleva Vera A., Pokrovsky Vadim S., Kukushkin Maxim E., Beloglazkina Elena K.
Журнал: International Journal of Molecular Sciences
Том: 25
Номер: 1
Год издания: 2024
Издательство: MDPI
Местоположение издательства: Basel, Switzerland
Номер статьи: 18
DOI: 10.3390/ijms25010018
Аннотация: 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.
Добавил в систему: Белоглазкина Елена Кимовна

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[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinedionesстатья

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