Mixed-ligand complexes of copper(I) with Schiff base and triphenylphosphine: Effective catalysts for the amination of aryl halide

Chavan, S.S.; Sawant, S.K.; Sawant, V.A.; Lahiri, Goutam Kumar

doi:10.1016/j.inoche.2011.05.025

Cited by 23 publications

(6 citation statements)

References 29 publications

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“…In the region between 1600–1450 cm –1 , the stretch bands of the CC and C–N bonds overlap . Vibrational modes typical of the triphenylphosphine ligand (P–C aromatic ) and stretching vibrations of the Cu–P bonds appear in the range of 500–430 cm –1 . − …”

Section: Resultsmentioning

confidence: 94%

Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

et al. 2021

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Six complexes with the general formula [Cu(acylthioureato)(PPh3)2] were synthesized and characterized using spectroscopic techniques (IR, UV/visible, and 1D and 2D NMR), mass spectrometry, elemental analysis, and X-ray diffraction. Interpretation of the in vitro cytotoxicity data of Cu(I) complexes took into account their stability in cell culture medium. DFT calculations showed that NMR properties, such as the shielding of carbon atoms, are affected by relativistic effects, supported by the ZORA Hamiltonian in the theoretical calculations. Additionally, the calculation of the energies of the frontier molecular orbitals predicted that the structural changes of the acylthiourea ligands did not cause marked changes in the reactivity descriptors. All complexes were cytotoxic to the evaluated tumor cell lines [MDA-MB-231 (triple-negative breast cancer, TNBC), MCF-7 (breast cancer), and A549 (lung cancer)]. In the MDA-MB-231 cell line, complex 1 significantly altered the cytoskeleton of the cells, reducing the density and promoting the condensation of F-actin filaments. In addition, the compound caused an increase in the percentage of cells in the fragmented DNA region (sub-G0) and induced cell death via the apoptotic pathway starting at the IC50 concentration. Taken together, the results show that complex 1 has cytotoxic and apoptotic effects on TNBC cells, which is a cell line originating from an aggressive, difficult-to-treat breast cancer.

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Section: Resultsmentioning

confidence: 94%

Experimental and Theoretical DFT Study of Cu(I)/N,N-Disubstituted-N′-acylthioureato Anticancer Complexes: Actin Cytoskeleton and Induction of Death by Apoptosis in Triple-Negative Breast Tumor Cells

et al. 2021

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“…One of the good precursors for the synthesis of potentially biologically active imine derivatives is 2-acetylpyridine. Besides the potential for medicinal application, Schiff bases of this ketone have a wide range of other uses, such as fluorescent and luminescent probes [34,35], optical sensors for determination of cadmium(II) in natural water and art-paint samples [36], effective catalysts [37], etc. The research has shown that imine derivatives of 2-acetylpyridine and their metal complexes express substantial in vitro activity against various human tumor lines [38,39] and significant cytotoxicity against some solid tumors and leukemia cells [40].…”

Section: Significance and Applicationmentioning

confidence: 99%

Some Aromatic Schiff Bases and Their Metal Complexes

Radanović¹,

Holló²

2023

Schiff Base in Organic, Inorganic and Physical Chemistry

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Schiff bases represent a widely studied group of compounds, interesting from the synthetic and structural, but also applicational point of view. Among these, aromatic Schiff bases stand out due to their stability and possible application as safer therapeutic agents. Since the presence of the phenolic group and the heteroatom in the benzene ring seems to be of interest for the biological activity of Schiff bases, imine derivatives of some dihydroxybenzaldehydes, 2-acetylpyridine, and 2,6-diacetylpyridine are chosen to be described here. The syntheses, structural features, as well as investigations of possible application of Schiff bases themselves, but also their metal complexes are described. The Cambridge Structural Database has been searched to obtain a better knowledge of the structures of these Schiff bases and their metal complexes, structural changes upon coordination, and the most common and interesting modes of coordination. The main accent is given to those compounds that are promising candidates for medicinal and pharmaceutical use, but some of the described complexes are good as catalysts, optical materials, sensors, analytical reagents, etc.

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“…For applications of Schiff base derivatives and their complexes, see: Chavan et al (2011); Ray et al (2011). For the crystal structures of related compounds, see: Nie (2008); Fun et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…Schiff bases have various applications in the study of biological processes and in pharmacology (Chavan et al, 2011;Ray et al, 2011). We report here the crystal structure of the title Schiff base compound (I).…”

Section: S1 Commentmentioning

confidence: 99%