Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones

Abstract

Synthesis, antioxidant activity, and quantitative structure-activity relationship (QSAR) of 25 of chalcone derivatives is reported here. They were synthesized by Claisen-Schmidt reaction and were characterized by FTIR, NMR, and mass spectroscopy. Antioxidant activity is evaluated through four different methods namely, superoxide radical-scavenging, hydrogen peroxide scavenging, reducing power, and DPPH radical-scavenging assays. Generally, compounds with -SCH 3 and -OCH 3 in the para position of the A-ring and -OH in the B-ring were more active than others. In few cases some of the compounds were more active than ascorbic acid or butylated hydroxytoluene. QSAR was developed correlating the antioxidant activity with the structural features of the compounds and the predictive capability of the models was estimated using internal and external validation methods. All the predictions were within the 99% confidence level. Spatial, structural, and lipophilic properties of the compounds determine their antioxidant properties.

Reactivity of phenolic compounds towards free radicals under in vitro conditions

“…The structure-antioxidant activity relationship (SAR) approach is considered to be useful for food, cosmetic and pharmaceutical applications as it provides evidence about the potency of natural phenolic constituents (Bountagkidou et al 2010). Bilto et al (2012), Sivakumar et al (2011), Bountagkidou et al (2010), Natella et al (1999) and Torres de Pinedo et al (2007) studied the SAR of flavonoids, chalcone derivatives, hydroxybenzaldehydes, benzoic and cinnamic acids and phenolic based antioxidants respectively employing different antioxidant assay methods. Cai et al (2006) studied the SAR of phenolic antioxidants from Chinese medicinal plants using ABTS and DPPH radical scavenging assays.…”

Comparative Study of Synthesis and Spectral Studies of Thiophenyl Carboxylate Derivatives by Microwave Irradiation and Conventional Method

“…Chalcones and its derivatives have attracted increasing attention due to numerous pharmacological applications. They have displayed a broad spectrum of pharmacological activities, among which antimalarial [1][2][3][4] , antifungal 5,6 , antimicrobial 7 , larvicidal 8 , anticonvulsant 9 , antioxidant [10][11][12] activities. The IR spectrum supported the data showing the characteristic band for C=O at 1645 to 1655 and C=C at around 1570 to 1600 cm -1 and aromatic CH band between 3000 to 3100 cm -1 and aliphatic CH band stretching between 2900 to 3000 cm -1 and band for the C-S group is in the range of 600 to 800 cm -1 .…”

Synthesis, Characterization and Antiinflammatory Activity of Chalcone Derivatives Linked with Apocynin and 5-Nitrofuran Moiety

“…They are significant as structural motifs among biologically active molecules and also for combinatorial assembly of heterocyclic scaffolds [2][3][4]. Chalcones containing several functional groups showed a wide spectrum of biological activities such as antileishmanial [5,6], antimalarial [5,7], anticancer [8,9], anti-HIV [10], antioxidant [11], inflammatory [12] antiprotozoal [13], antiulcer [14] and antimicrobial [15,16] activities.…”