Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach

Milovanović, Vesna; Petrović, Zorica D.; Novaković, Slađana B.; Bogdanović, Goran A.; Petrović, Vladimir P.; Simijonović, Dušica

doi:10.1016/j.tet.2020.131456

Cited by 10 publications

(8 citation statements)

References 64 publications

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“…All chemicals were acquired either from Sigma-Aldrich Co. or Merck & Co. Benzohydrazides (1)(2)(3)(4)(5) were prepared according to the previously reported method [43]. The IR spectra were recorded on a PerkinElmer Spectrum One FT-IR spectrometer using the KBr plates.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of antioxidant and cytotoxic properties of phenolic N -acylhydrazones: structure–activity relationship

et al. 2022

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Cancer is still a relentless public health issue. Particularly, colorectal cancer is the third most prevalent cancer in men and the second in women. Moreover, cancer development and growth are associated with various cell disorders, such as oxidative stress and inflammation. The quest for efficient therapeutics is a challenging task, especially when it comes to achieving both cytotoxicity and selectivity. Herein, five series of phenolic N -acylhydrazones were synthesized and evaluated for their antioxidant potency, as well as their influence on HCT-116 and MRC-5 cells viability. Among 40 examined analogues, 20 of them expressed antioxidant activity against the DPPH radical. Furthermore, density functional theory was employed to estimate the antioxidant potency of the selected analogues from the thermodynamical aspect, as well as the preferable free-radical scavenging pathway. Cytotoxicity assay exposed enhanced selectivity of a number of analogues toward cancer cells. The structure–activity analysis revealed the impact of the type and position of the functional groups on both cell viability and selectivity toward cancer cells.

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Section: Methodsmentioning

confidence: 99%

Evaluation of antioxidant and cytotoxic properties of phenolic N -acylhydrazones: structure–activity relationship

et al. 2022

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“…Chemicals (purity > 98%) used for the synthesis were acquired from Merck, and vinegar (acetic acid 90 g/L) was purchased from the local market. Compounds 3-acetyl-4-hydroxycoumarin (1) and hydrazides (2) were prepared according to the previously reported methods [19,20]. All chemicals used in HPLC analysis were HPLC grade.…”

Section: Chemical Reagents and Instrumentsmentioning

confidence: 99%

Green One-Pot Synthesis of Coumarin-Hydroxybenzohydrazide Hybrids and Their Antioxidant Potency

et al. 2021

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Compounds from the plant world that possess antioxidant abilities are of special importance for the food and pharmaceutical industry. Coumarins are a large, widely distributed group of natural compounds, usually found in plants, often with good antioxidant capacity. The coumarin-hydroxybenzohydrazide derivatives were synthesized using a green, one-pot protocol. This procedure includes the use of an environmentally benign mixture (vinegar and ethanol) as a catalyst and solvent, as well as very easy isolation of the desired products. The obtained compounds were structurally characterized by IR and NMR spectroscopy. The purity of all compounds was determined by HPLC and by elemental microanalysis. In addition, these compounds were evaluated for their in vitro antioxidant activity. Mechanisms of antioxidative activity were theoretically investigated by the density functional theory approach and the calculated values of various thermodynamic parameters, such as bond dissociation enthalpy, proton affinity, frontier molecular orbitals, and ionization potential. In silico calculations indicated that hydrogen atom transfer and sequential proton loss–electron transfer reaction mechanisms are probable, in non-polar and polar solvents respectively. Additionally, it was found that the single-electron transfer followed by proton transfer was not an operative mechanism in either solvent. The conducted tests indicate the excellent antioxidant activity, as well as the low potential toxicity, of the investigated compounds, which makes them good candidates for potential use in food chemistry.

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“…Based on the calculated reaction enthalpies (ΔH BDE , ΔH IP , ΔH PDE , ΔH PA , and The hydroxy benzohydrazides were synthesized starting from the corresponding methyl esters and hydrazine monohydrate according to the previously reported method. [57] The 1 H NMR and 13 The synthesis of the compounds a-n was performed using a previously reported method. [34] Here, the hydroxy benzohydrazide was mixed with equimolar amounts of the corresponding aromatic aldehyde in ethanol as solvent.…”

Section: Discussionmentioning

confidence: 99%

“…The hydroxy benzohydrazides were synthesized starting from the corresponding methyl esters and hydrazine monohydrate according to the previously reported method. [ 57 ] The 1 H NMR and 13 C NMR spectra were recorded on a Varian Gemini spectrometer (200 MHz for 1 H and 50 MHz for 13 C) in chloroform (CDCl 3 ) and dimethyl sulfoxide‐ d 6 (dimethyl sulfoxide [DMSO]‐ d 6 ) as solvents. The UV–Vis spectra were measured on the Agilent Technologies, Cary 300 Series UV–Vis Spectrophotometer within the 200–600 nm range, which was also employed in the antioxidant activity assays.…”

Section: Methodsmentioning

confidence: 99%

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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Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach

Cited by 10 publications

References 64 publications

Evaluation of antioxidant and cytotoxic properties of phenolic N -acylhydrazones: structure–activity relationship

Evaluation of antioxidant and cytotoxic properties of phenolic N -acylhydrazones: structure–activity relationship

Green One-Pot Synthesis of Coumarin-Hydroxybenzohydrazide Hybrids and Their Antioxidant Potency

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

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