Novel complexes with ONNO tetradentate coumarin schiff-base donor ligands: x-ray structures, DFT calculations, molecular dynamics and potential anticarcinogenic activity

Mestizo, Paula Daniela; Narváez, Diana; Pinzón-Ulloa, Jesús Alberto; Bello, Daniela Torres Di; Franco-Ulloa, Sebastian; Macías, Mario A.; Groot, Helena; Miscione, Gian Pietro; Suescun, Leopoldo; Hurtado, John

doi:10.1007/s10534-020-00268-8

Cited by 16 publications

(8 citation statements)

References 71 publications

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“…Synthesis and Characterization of L3. The compounds A, L1, and L2 (Figure 2) were synthesized following previously reported methodologies, 20,21 and L3 had not been reported. However, it was synthesized similarly by the double condensation reaction between 4,5-dichloro-o-phenylenediamine and 8-formyl-7-hydroxycoumarin.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…19 In this context, we focused our efforts on the synthesis of a series of organocatalytic coumarin derivatives (L1, L2, and L3). Although salophen-type bisphenol compounds have recently been reported as organocatalysts, coumarin-derived compounds, although they are "salophen-type bisphenol compounds", are a completely different family of compounds and due to their specific structure, they present very particular steric and electronic characteristics, 20 which make them suitable candidates for studies as performed in this article. These catalysts were used to carry out catalytic screening with terminal epoxides (1a−k) and cyclohexene oxide (1l).…”

Section: ■ Introductionmentioning

confidence: 99%

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Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions

Fonseca-López,

Ezenarro-Salcedo,

Zapata-Rivera

et al. 2024

ACS Omega

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8-Formyl-7-hydroxycoumarin (A) and their derived salophen-type organocatalysts L1, L2, and L3 were used for the synthesis of cyclic carbonates from carbon dioxide (CO2) and epoxides under solvent-, halide-, and metal-free conditions. According to previous optimization tests, L1 and L2 had the best catalytic activity presenting 89 and 92% conversion toward the synthesis of 3-chloropropylene carbonate (2c) using 8 bar CO2, 100 °C at 9 h. Therefore, they were used as organocatalysts to complete the catalytic screening with 11 terminal epoxides (1a–k) exhibiting the highest TOF values of 20 and 22 h–1 using 1c and 1b, respectively. Similarly, they were tested with an internal epoxide, such as cyclohexene oxide (1l) exhibiting 72% conversion, becoming the first salophen organocatalyst to obtain cis-cyclohexane carbonate (2l) in the absence of a cocatalyst. In addition, a reaction mechanism was proposed for the formation of cyclic carbonates based on experimental data and computational techniques; these contributed in establishing a probable role of CO2 pressure along the catalysis and the hydrogen bonds that favor the stabilization of the different intermediates of the reaction.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions

Fonseca-López,

Ezenarro-Salcedo,

Zapata-Rivera

et al. 2024

ACS Omega

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“…Ulukaya and co-workers presented results of very potent anticancer activity of tested palladium(II) complex against breast carcinoma cells with IC 50 values of 0.09 μM for MDA-MB-231 and 3.05 μM for MCF-7 cells [ 26 ]. The literature data reveals many coumarin-metal based complexes with antitumor activity, [ 28 , 29 , 30 ], however, this is the first report on coumarin palladium(II) complex anticancer activity against pancreatic adenocarcinoma cells.…”

Section: Discussionmentioning

confidence: 99%

Coumarin-Palladium(II) Complex Acts as a Potent and Non-Toxic Anticancer Agent against Pancreatic Carcinoma Cells

et al. 2022

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Pancreatic carcinoma still represents one of the most lethal malignant diseases in the world although some progress has been made in treating the disease in the past decades. Current multi-agent treatment options have improved the overall survival of patients, however, more effective treatment strategies are still needed. In this paper we have characterized the anticancer potential of coumarin-palladium(II) complex against pancreatic carcinoma cells. Cells viability, colony formation and migratory potential of pancreatic carcinoma cells were assessed in vitro, followed by evaluation of apoptosis induction and in vivo testing on zebrafish. Presented results showed remarkable reduction in pancreatic carcinoma cells growth both in vitro and in vivo, being effective at micromolar concentrations (0.5 μM). Treatments induced apoptosis, increased BAX/BCL-2 ratio and suppressed the expression of SOX9 and SOX18, genes shown to be significantly up-regulated in pancreatic ductal adenocarcinoma. Importantly, treatments of the zebrafish-pancreatic adenocarcinoma xenografts resulted in significant reduction in tumor mass, without provoking any adverse toxic effects including hepatotoxicity. Presented results indicate the great potential of the tested compound and the perspective of its further development towards pancreatic cancer therapy.

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“…Remarkable examples of novel cobalt (II) complexes have been presented by Mestizo and collaborators ( Mestizo et al, 2021 ). Complexes 7 and 8 ( Table 1 ) were synthesized starting from two tetradentate ligands bearing coumarin Schiff base (R = H, OCH 3 ) and further evaluated against human cervical epithelioid carcinoma cell line (HeLa) and non-carcinogenic human cell lines (HFF-1 and HaCaT).…”

Section: Anticancer Complexesmentioning

confidence: 98%

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

et al. 2021

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The coumarin nucleus is a recurring motif in both natural and synthetic compounds that exhibit a broad spectrum of biological properties including anticoagulant, anti-inflammatory, antioxidant, antiviral, antimicrobial and anticancer agents as well as enzyme inhibitors. On the other hand, it has been reported that the incorporation of a metal ion into coumarin derivatives can increase the activity of such complexes compared to coumarin-based ligands. Accordingly, some of them have been found to display promising antioxidant, antitumor or antibacterial activities. This mini-review briefly summarizes the recent development of coumarin-metal complexes with proven biological properties. The attention is also paid to agents for which practical applications in the detection of biologically important species may be found.

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Novel complexes with ONNO tetradentate coumarin schiff-base donor ligands: x-ray structures, DFT calculations, molecular dynamics and potential anticarcinogenic activity

Cited by 16 publications

References 71 publications

Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions

Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions

Coumarin-Palladium(II) Complex Acts as a Potent and Non-Toxic Anticancer Agent against Pancreatic Carcinoma Cells

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

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Novel complexes with ONNO tetradentate coumarin schiff-base donor ligands: x-ray structures, DFT calculations, molecular dynamics and potential anticarcinogenic activity

Cited by 16 publications

References 71 publications

Salophen-type Organocatalysts for the Cycloaddition of CO2 and Epoxides under Solvent, Halide, and Metal-Free Conditions

Salophen-type Organocatalysts for the Cycloaddition of CO2 and Epoxides under Solvent, Halide, and Metal-Free Conditions

Coumarin-Palladium(II) Complex Acts as a Potent and Non-Toxic Anticancer Agent against Pancreatic Carcinoma Cells

A Mini-Review: Recent Advances in Coumarin-Metal Complexes With Biological Properties

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Product

Resources

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Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions

Salophen-type Organocatalysts for the Cycloaddition of CO₂ and Epoxides under Solvent, Halide, and Metal-Free Conditions