Structure and photoisomerization studies of a new spiropyran with azomethine fragment

Pugachev, A.D.; Ozhogin, I.V.; Kozlenko, A.S.; Makarova, N.I.; Rostovtseva, I.A.; Dmitriev, V.S.; Borodkin, G.S.; Laptieva, D.S.; Tkachev, V.V.; Utenyshev, A.N.; Metelitsa, A.V.; Aldoshin, S.M.; Lukyanov, B.S.

Авторы: Pugachev Artem D., Ozhogin Ilya V., Kozlenko Anastasiia S., Makarova Nadezhda I., Rostovtseva Irina A., Dmitriev Vitaly S., Borodkin Gennady S., Laptieva Diana S., Tkachev Valery V., Utenyshev Andrey N., Metelitsa Anatoly V., Aldoshin Sergey M., Lukyanov Boris S.
Журнал: Structural Chemistry
Год издания: 2026
Издательство: Springer-Verlag
Местоположение издательства: Heidelberg, Germany
DOI: 10.1007/s11224-026-02740-6
Аннотация: This study focuses on the synthesis of a new spiropyran with an azomethine moiety. The synthesis was carried out by a condensation reaction between formyl-substituted spiropyran and para-anisidine. A detailed study using NMR, FT-IR, and mass spectroscopy was carried out to confirm the structure of the resulting azomethine. Particular attention was paid to single crystal X-ray diffraction analysis. Hirshfeld surface calculations were performed to elucidate the nature and relative contributions of the intermolecular interactions that govern crystal packing. Since the molecule has two fragments prone to photoisomerization, one of the main objectives of the study was to study its behavior under UV irradiation. Establishing the relationship between the structure and properties of such compounds is an important and actual task for the molecular design of organic photochromes. During spectral-kinetic studies the target compound showed unexpected photochromic behavior different from standard formation of a merocyanine isomer. With support of quantum chemical calculations, the predominant photoactivation path through azometine fragment cis-trans isomerization was established. Due to the fact that the molecule contains several structural fragments that determine its potential activity against bacteria and biofilms, as well as the inhibition of β-secretase, we have given a preliminary assessment of the prospects for using the resulting azomethine for pharmaceutical purposes using the molecular docking method.
Добавил в систему: Алдошин Сергей Михайлович

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Structure and photoisomerization studies of a new spiropyran with azomethine fragmentстатья