Synthesis and structural characterization of novel O-substituted phenolic and chalcone derivatives with antioxidant activity
Open Access
- 22 June 2020
- journal article
- research article
- Published by SAGE Publications in Journal of Chemical Research
- Vol. 45 (1-2), 159-165
- https://doi.org/10.1177/1747519820932789
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 µg/mL) had moderate antioxidant activity.Keywords
Funding Information
- Funding of Visiting Scientists on Sabbatical Leave Fellowship Program (TÜBITAK-BIDEB 2221)
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