Structural correlation of some heterocyclic chalcone analogues and evaluation of their antioxidant potential

• Published in: Molecules (Basel, Switzerland) Vol. 18; no. 10; pp. 11996 - 12011
• Main Authors: Kumar, C S Chidan, Loh, Wan-Sin, Ooi, Chin Wei, Quah, Ching Kheng, Fun, Hoong-Kun
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 26-09-2013; MDPI
• Subjects: Antioxidants; Benzothiazoles - chemistry; Biphenyl Compounds - chemistry; Chalcones - chemistry; Copper - chemistry; Crystallography, X-Ray; Ferricyanides - chemistry; Free Radical Scavengers - chemistry; Free Radicals - chemistry; heterocyclic; Models, Molecular; Molecular Conformation; overlay; Oxidation-Reduction; Picrates - chemistry; radical scavenging; reducing; Single crystals; substituent; Sulfonic Acids - chemistry
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules181011996

A series of six novel heterocyclic chalcone analogues 4(a-f) has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC₀ values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent.