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New palladium complexes based on myrtenal and benzylamine derivatives: Selectivity of cyclometalation, antitumor activity

[Display omitted] •The synthesis of new palladium complexes with terpene ligands is presented.•The study of the toxic effect was carried out on various cell lines of tumor.•The ability of palladacycles to suppress the proliferative potential of cells of tumor origin was revealed. (1R,5S)-(–)-Myrtena...

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Published in:Inorganica Chimica Acta 2025-02, Vol.576, p.122457, Article 122457
Main Authors: Zalevskaya, O.A., Gur’eva, Y.A., Kutchin, A.V., Aleksandrova, Yu.R., Pukhov, S.A., Nikolaeva, N.S., Neganova, M.E.
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container_title Inorganica Chimica Acta
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creator Zalevskaya, O.A.
Gur’eva, Y.A.
Kutchin, A.V.
Aleksandrova, Yu.R.
Pukhov, S.A.
Nikolaeva, N.S.
Neganova, M.E.
description [Display omitted] •The synthesis of new palladium complexes with terpene ligands is presented.•The study of the toxic effect was carried out on various cell lines of tumor.•The ability of palladacycles to suppress the proliferative potential of cells of tumor origin was revealed. (1R,5S)-(–)-Myrtenal and benzylamine derivatives were synthesized as ligands. The cyclopalladation of the resulting benzyl imines and amines was studied for the first time. High regioselectivity of the cyclometalation of myrtenal benzylimines was shown – under all conditions studied, the vinyl proton is replaced with the formation of Csp2-palladacycles. In the case of amines the result of the palladation reaction depends significantly on the conditions. When palladium acetate is used, the reaction is complicated by the dehydrogenation of amines to the corresponding imines and the cyclopalladation of the latter. Ortho-palladation on the aromatic ring is possible only in the case of amine containing an α-methylbenzylamine moiety. All new compounds were characterized by NMR, IR spectroscopy, and elemental analysis. When studying the biological activity of the synthesized complexes revealed the ability of palladacycles based on myrtenal and benzylamine derivatives to reduce the viability of cells of tumor origin, as well as to inhibit the the proliferative potential of cells, which may be related to the ability to cause apoptosis induction.
doi_str_mv 10.1016/j.ica.2024.122457
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subjects Antitumor activity
Apoptosis induction
Benzylamine
Cyclometallation
Migration activity
Myrtenal
Palladium complexes
Proliferative potential
title New palladium complexes based on myrtenal and benzylamine derivatives: Selectivity of cyclometalation, antitumor activity
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