Vanillic Mannich bases: synthesis and screening of biological activity. Mechanistic insight into the reaction with 4-chloroaniline

Petrović, Vladimir P.; Simijonović, Dušica; Živanović, Marko; Košarić, Jelena V.; Petrović, Zorica D.; Marković, Svetlana; Marković, Snežana D.

doi:10.1039/c4ra03909b

Cited by 25 publications

(18 citation statements)

References 58 publications

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“…In our previous study, catalytic role of monoethanolamine, diethanolamine and N,N-diethylethanolamine chloroacetates in the Mannich reaction was presented (Petrović et al, 2014). The present paper describes the catalytic role of triethanolammonium chloroacetate ([HTEA] [ClAc]) in the reaction of vanillin, aniline and cyclohexanone.…”

Section: Resultsmentioning

confidence: 99%

“…yielded MB-H, which was analyzed by 1 H NMR, 13 C NMR and IR spectroscopy. All spectroscopic data as well as the ESI-MS spectrometric data were presented in our previous study (Petrović et al, 2014).…”

Section: Methodsmentioning

confidence: 99%

“…Taking into account that the present study is an extension of our recent work (Petrović et al, 2014), the same level of theory was applied to achieve compatibility of the results. Geometrical parameters of all stationary points in ethanol (ε = 24.3) were optimized using the conductor-like solvation model (CPCM) (Barone & Cossi, 1998;Cossi et al, 2003).…”

Section: Theoreticalmentioning

confidence: 99%

“…However, there are very limited data on the Mannich-type reactions catalyzed by ILs from biologically relevant ethanolamines (Abbott et al, 2002). Recently, details on the Mannich reaction catalyzed by some ethanolamine based ILs have been reported (Petrović et al, 2014). Excellent diastereoselectivity of the examined reactions was observed.…”

Section: Introductionmentioning

confidence: 99%

“…For this purpose, the reaction of aniline, vanillin, and cyclohexanone catalyzed by triethanolammonium chloroacetate ([HTEA][ClAc]) was examined using experimental and theoretical tools. Such selection was based on the fact that the reactions performed in the presence of this IL exhibited slightly higher yields in comparison to those presented in Petrović et al (2014).…”

Section: Introductionmentioning

confidence: 99%

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Formation of a vanillic Mannich base – theoretical study

et al. 2015

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One-pot anti-Mannich reaction of vanillin, aniline and cyclohexanone was successfully catalyzed by ionic liquid triethanolammonium chloroacetate, at room temperature. Yield of the obtained Mannich base was very good and excellent diastereoselectivity was achieved. Mechanism of the reaction was investigated using the density functional theory. The reaction started with a nucleophilic attack of aniline nitrogen at the carbonyl group of vanillin. The intermediate α-amino alcohol formed in this way was further subjected to protonation by the triethanolammonium ion yielding the imminium ion. Theoretically, the obtained imminium ion and the enol form of cyclohexanone can build the protonated Mannich base via the anti and syn pathways. The chloroacetic anion spontaneously abstracts the proton yielding the final product of the reaction anti 2-[1-(N-phenylamino)-1-(4-hydroxy-3-methoxyphenyl)]methylcyclohexanone (MB-H). The syn pathway requires lower activation energy but the anti pathway yields a thermodynamically more stable product, which implies that the examined Mannich reaction is thermodynamically controlled.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Theoreticalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Formation of a vanillic Mannich base – theoretical study

et al. 2015

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Structure, interaction with biomolecules, and cytotoxicity of copper (II) complexes chelating some Schiff base ligands

Mijatović,

Caković,

Lolić

et al. 2023

Applied Organom Chemis

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Cancer remains one of the most common diseases worldwide in terms of deaths and claims many lives every day. Transition metal complexes are candidates in the development of anticancer drugs, with cisplatin being used in chemotherapy worldwide. Copper, an endogenous metal, is known for its pronounced redox potential and nucleophilicity, especially when bound to biological molecules. Cu (II) complexes were synthesized containing ethane‐1,2‐diamine as amine moiety and pentane‐2,4‐dione and/or 1‐phenylbutane‐1,3‐dione, pentane‐2,4‐dione and/or 1,1,1‐trifluoropentane‐2,4‐dione or 1,1,1‐trifluoropentane‐2,4‐dione and/or 1‐phenylbutane‐1,3‐dione as β‐diketone moiety. Standard methods were used to confirm the structure of complexes 1–6. X‐ray crystal structure analysis characterized complex 1 containing the ligand ethane‐1,2‐diamine and pentane‐2,4‐dione. The interactions of complexes 1–6 with calf thymus DNA (ct‐DNA) were followed by electronic absorption and fluorescence spectroscopy methods and by viscosity measurements. In contrast, interaction with Salmon Sperm DNA was investigated using the electrophoretic mobility shift assay. The results indicate a moderate affinity of complexes 1–6 for binding to DNA. Gel electrophoresis also shows that the studied complexes have a concentration‐dependent interaction with DNA. Spectroscopic fluorescence techniques were used to monitor the affinity of the complexes for bovine serum albumin (BSA). Complexes 1–6 showed satisfactory binding ability for BSA. Cytotoxicity analyses were performed on the human colorectal carcinoma HCT‐116 and healthy lung fibroblast MRC‐5 cell lines, showing that complex 5 exhibited selectivity between cancer and normal cells, which is critical for drug development.

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Novel N‐pyrocatechoyl and N‐pyrogalloyl hydrazone antioxidants endowed with cytotoxic and antibacterial activity

Branković,

Matejić,

Simijonović

et al. 2024

Archiv der Pharmazie

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Over the years, pharmacological agents bearing antioxidant merits arose as beneficial in the prophylaxis and treatment of various health conditions. Hazardous effects of radical species hyperproduction disrupt normal cell functioning, thus increasing the possibility for the development of various oxidative stress‐associated disorders, such as cancer. Contributing to the efforts for efficient antioxidant drug discovery, a thorough in vitro and in silico assessment of antioxidant properties of 14 newly synthesized N‐pyrocatechoyl and N‐pyrogalloyl hydrazones (N‐PYRs) was accomplished. All compounds exhibited excellent antioxidant potency against the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical. The extensive in silico analysis revealed multiple favorable features of N‐PYRs to inactivate harmful radical species, which supported the obtained in vitro results. Also, in silico experiments provided insights into the preferable antioxidant pathways. Prompted by these findings, the cytotoxicity effects and the influence on the redox status of cancer HCT‐116 cells and healthy fibroblasts MRC‐5 were evaluated. These investigations exposed four analogs exhibiting both cytotoxicity and selectivity toward cancer cells. Furthermore, the frequently uncovered antimicrobial potency of hydrazone‐type hybrids encouraged investigations on G+ and G– bacterial strains, which revealed the antibacterial potency of several N‐PYRs. These findings highlighted the N‐PYRs as excellent antioxidant agents endowed with cytotoxic and antibacterial features.

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Vanillic Mannich bases: synthesis and screening of biological activity. Mechanistic insight into the reaction with 4-chloroaniline

Abstract: Vanillic Mannich bases were catalytically synthesized, and their cytotoxic and antioxidative activities examined.

Cited by 25 publications

References 58 publications

Formation of a vanillic Mannich base – theoretical study

Formation of a vanillic Mannich base – theoretical study

Structure, interaction with biomolecules, and cytotoxicity of copper (II) complexes chelating some Schiff base ligands

Novel N‐pyrocatechoyl and N‐pyrogalloyl hydrazone antioxidants endowed with cytotoxic and antibacterial activity

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