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Synthesis of new allylidene amino phenol-containing Schiff bases and metal complex formation using trimethinium salts.

ABSTRACT: An efficient route for the synthesis of novel Schiff bases from the condensation reaction of 2-substituted 1,3-bis(dimethylamino)-trimethinium salts with diverse aminophenols in the presence of triethylamine in EtOH at reflux is described. Complexes of transition metals with Schiff base ligand (L) 3c, having the donor atom set N₂O₂, were studied. The ultraviolet spectral behavior of the complexes in DMSO was investigated and the λ _max of these compounds was examined. The structure of the new compounds was confirmed based on their spectral data from IR, ¹H NMR and ¹³C NMR, mass spectra, and elemental analysis.

SUBMITTER: Rafiee Samani Z

PROVIDER: S-EPMC9034104 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Synthesis of new allylidene amino phenol-containing Schiff bases and metal complex formation using trimethinium salts.

Rafiee Samani Ziba Z Mehranpour Abdolmohammad A

RSC advances 20210618 35

An efficient route for the synthesis of novel Schiff bases from the condensation reaction of 2-substituted 1,3-bis(dimethylamino)-trimethinium salts with diverse aminophenols in the presence of triethylamine in EtOH at reflux is described. Complexes of transition metals with Schiff base ligand (L) 3c, having the donor atom set N2O2, were studied. The ultraviolet spectral behavior of the complexes in DMSO was investigated and the λ max of these compounds wa ...[more]

PMID: 35478780

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Project description:The widespread usage of Schiff bases in chemistry, industry, medicine, and pharmacy has increased interest in these compounds. Schiff bases and derivative compounds have important bioactive properties. Heterocyclic compounds containing phenol derivative groups in their structure have the potential to capture free radicals that can cause diseases. In this study, we designed and synthesized eight Schiff bases (10-15) and hydrazineylidene derivatives (16-17), which contain phenol moieties and have the potential to be used as synthetic antioxidants, for the first time using microwave energy. Additionally, the antioxidant effects of Schiff bases (10-15) and hydrazineylidene derivatives (16-17) were studied using by the bioanalytical methods of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical (ABTS•+) and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) scavenging activities, and Fe3+, Cu2+, and Fe3+-TPTZ complex reducing capacities. In the context of studies on antioxidants, Schiff bases (10-15) and hydrazineylidene derivatives (16-17) were found to be as powerful DPPH (IC50: 12.15-99.01 μg/mL) and ABTS•+ (IC50: 4.30-34.65 μg/mL). Additionally, the inhibition abilities of Schiff bases (10-15) and hydrazineylidene derivatives (16-17) were determined towards some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCAs I and II), enzymes that are linked to some global disorders including Alzheimer's disease (AD), epilepsy, and glaucoma. In the context of studies on enzyme inhibition, it was observed that the synthesized Schiff bases (10-15) and hydrazineylidene derivatives (16-17) inhibited AChE, BChE, hCAs I, and hCA II enzymes with IC50 values in ranges of 16.11-57.75 nM, 19.80-53.31 nM, 26.08 ± 8.53 nM, and 85.79 ± 24.80 nM, respectively. In addition, in light of the results obtained, we hope that this study will be useful and guiding for the evaluation of biological activities in the fields of the food, medical, and pharmaceutical industries in the future.

Dataset Information

Synthesis of new allylidene amino phenol-containing Schiff bases and metal complex formation using trimethinium salts.

Publications

Synthesis of new allylidene amino phenol-containing Schiff bases and metal complex formation using trimethinium salts.

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