Novel binuclear copper(II) complexes with sulfanylpyrazole ligands: synthesis, crystal structure, fungicidal, cytostatic, and cytotoxic activity.

New binuclear copper(II) [Cu(II)] tetraligand complexes (six examples) with sulfanylpyrazole ligands were synthesized. Electron spin resonance (ESR) studies have shown that in solution the complexes are transformed to the mononuclear one. Fungicidal properties against Candida albicans were found for the Cu complexes with benzyl and phenyl substituents. An in vitro evaluation of the cytotoxic properties of Cu chelates against HEK293, Jurkat, MCF-7, and THP-1 cells identified the Cu complex with the cyclohexylsulfanyl substituent in the pyrazole core as the lead compound, whereas the Cu complex without a sulfur atom in the pyrazole ligand had virtually no cytotoxic or fungicidal activity. The lead Cu(II) complex was more active than cisplatin. Effect of the S-containing Cu complex on apoptosis and cell cycle distribution has been investigated as well.

2-Amino-3,5-dicarbonitrile-6-sulfanylpyridines: synthesis and multiple biological activity - a review.

This review integrates the published data of the last decade (from 2010 to 2020) on the synthesis of the 2-amino-3,5-dicarbonitrile-6-sulfanylpyridine scaffold, the derivatives of which are widely used in the synthesis of biologically active compounds. Currently, no systematic accounts of synthetic routes towards this class of heterocyclic compounds can be found in the literature. The present-day trends in the catalytic synthesis of 2-amino-3,5-dicarbonitrile-6-sulfanylpyridines are considered using pseudo-four-component reaction (pseudo-4CR) by condensation of malononitrile molecules with thiols and aldehydes, and alternative three-component (3CR) condensations of malononitrile with 2-arylidenemalononitrile and S-nucleophiles.

Metal-free multicomponent synthesis of novel macrocyclic tetrathiadienes with cyano and amino groups.

The first synthesis of 5,12-diamino-7,14-bis(aryl)-1,4,8,11-tetrathiacyclotetradeca-5,12-diene-6,13-dicarbonitriles was performed as a multicomponent macroheterocyclization of malononitrile, aryl aldehydes, and 1,2-ethanedithiol in the presence of a catalytic amount of triethylamine in ethanol. The structures of the obtained macroheterocycles were confirmed by spectral methods, X-ray diffraction, and MALDI TOF mass spectrometry.

Synthesis of new N,N'-Pd(Pt) complexes based on sulfanyl pyrazoles, and investigation of their in vitro anticancer activity.

The synthesis of new N,N'-mononuclear bi-ligand Pd(ii) and tri-ligand Pt(ii)complexes bearing sulfanyl(phenyl, benzyl, cyclohexyl, 4-hydroxyphenyl)3,5-dimethyl-1H-pyrazole ligands has been carried out. The obtained compounds were studied for apoptosis-inducing activity and effect on the cell cycle for Jurkat, K562, and U937 neoplastic cell cultures and conditionally normal human embryonic kidney HEK293 cells. The cells showed the highest sensitivity to platinum and palladium complexes in comparison with ligands and cisplatin. The cytotoxic properties are enhanced for compounds with cyclohexyl substituents at the S-atom in sulfanyl pyrazoles and complexes.