Article 2021 · 5 citations

Synthesis and structural characterization of novel<i>O</i>-substituted phenolic and chalcone derivatives with antioxidant activity

Ngameni, Bathelemy, Erdogan, Musa, Kuete, Victor, Dalkilic, Erdin, Ngadjui, Bonaventure T., Dastan, Arif

Abstract

A series of novel 4-O-alkyltriazolylphenolic derivatives is first synthesized with good to excellent yields via the click reaction of 3-methoxy-4-O-propargylbenzaldehyde or 3-allyl-4-O-propargylacetophenone and aromatic azide derivatives. Next, the chalcones are prepared via the Claisen-Schmidt method from 4-O-alkylphenylketone derivatives in the presence of the corresponding (hetero)aromatic aldehydes as electrophiles. The structures of the newly synthesized compounds are confirmed from their infrared, nuclear magnetic resonance spectral data, and by elemental analysis. The main advantages of this procedure are the simplicity of the reaction conditions, easily available starting materials, and simple work-up. The antioxidant activity of several of the products is determined using the DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) radical scavenging assay. 4-O-propargylvanillin (IC50 = 14.54 mu g/mL) had moderate antioxidant activity.

Keywords

1 3-dipolar cycloaddition antioxidant activity click chemistry condensation reaction O-alkylation triazolated derivatives BIOLOGICAL-ACTIVITY AZIDES 1,2,3-TRIAZOLES DESIGN POTENT

WoS Categories

Chemistry, Multidisciplinary

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF CHEMICAL RESEARCH
Year: 2021
Volume: 45
Issue: 1-2
Pages: 159-165
ISSN: 1747-5198
eISSN: 2047-6507
DOI: 10.1177/1747519820932789
WoS UID: WOS:000558138900001

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