Structural Correlation of Some Heterocyclic Chalcone Analogues and Evaluation of Their Antioxidant Potential

Abstract

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 IC 50 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.

(2E,2′E)-1,1′-(1,4-Phenylene)bis[3-(3-chlorophenyl)prop-2-en-1-one]

“…Crystalline chalcone derivatives are also of interest due to their second and third harmonic generation properties (Chidan et al, 2015). The optical properties of the molecules are also associated with their molecular geometry (Kumar et al 2013) and, as a part of our ongoing work on such molecules (Naveen et al 2017), we report here the crystal structure of the title compound. The title compound crystallizes with one half-molecule in the asymmetric unit and its structure is shown in Fig.…”

Conformational studies of 2-(4-bromophenyl)-2-oxoethyl benzoates

“…The ability of the test samples, in addition to the standard anti-oxidant butylated hydroxyltoluene (BHT), on DPPH radical scavenging was estimated according to the method described earlier [14,15]. Compounds of different concentrations were prepared in ethanol, 1 mL of each compound solution having different concentrations (10-250 μg/mL).…”

(E)-1-(3-Bromophenyl)-3-(4-nitrophenyl)prop-2-en-1-one

“…They are also considered to be the precursors of flavonoids and isoflavonoids. Owing to their electronic structure, chalcones also find unique applications as fluorescent probes for sensing metal ions (Kumar et al 2013). In a continuation of our work on the synthesis of new chalcones and studies of their NLO properties (Tejkiran et al, 2016;Chidan et al 2016), we report here the crystal structure of the title compound.…”