Improvement of antioxidative activity of resveratrol by calix[4]arene-like tetramer: A theoretical study

Antiradical and Antioxidative Activity of Azocalix[4]arene Derivatives: Combined Experimental and Theoretical Study

“…Quantum mechanical methods have also been extensively used for evaluating the O–H BDE [26,27]. In this present work, DFT calculations have been performed at the BP86/6-311+G(d,p) level of theory to calculate the O–H BDEs and the PAs of phenolate anions of azocalixarene derivatives 1 and 2 in an aqueous solution in order to explore the antiradical and antioxidative mechanisms [12,28]. For comparison, the O–H BDEs of calix[4]arene, p -carboxyphenyl-azo-phenol and 3-aminopyridine-azo-phenol and the PAs of phenolate anions of them are also calculated.…”

“…Four dihydropyrimidine moieties were grafted at the upper rim of calix[4]arene, which produced calix[4]arene-based dihydropyrimidines that possess amplified antiradical activity in comparison to the corresponding monomers [11]. Furthermore, a calix[4]arene-like tetramer of resveratrol was reported to exhibit significantly improved antioxidative activity with respect to resveratrol [12]. Calixarene-based antioxidant C-methylcalix[4]resorcinarene also exhibited superior antioxidative efficiency in natural rubber vulcanizates compared to that of classical antioxidant 2,6-di-tert-butyl-4-methylphenol (BHT) [13].…”

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

“…However, only recently, Silva et al reported the novel iminecalix [4]arene derivatives (42-47) with anticandidal activity (Scheme 3) [55]. However, there are Lu et al reported the theoretical study that allowed one to find a way for improving the antioxidative activity of resveratrol by calix [4]arene-like tetramer [51]. In this study, they designed tetra-(3,5-dihydroxy)styryl-calix [4]arene (36, a calix [4]arene-like tetramer of resveratrol) and theoretically studied at the DFT-BP86/6-311+G(d,p) level of theory for antioxidant activity in comparison to resveratrol 37 ( Figure 6).…”

“…General scheme for the synthesis of resorcinarene derivatives.In 2009, Vovk et al reported on the antioxidant and antiradical activities of resorcinarene tetranitroxides (Figure 8)[67]. They synthesized the resorcinarene(48,49) derivatives(50)(51)(52)(53) by the aminomethylation of resorcinarene octols with 4-amino-TEMPO TEMPO ((4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl), and studied their antioxidant activities. They found that the Tetra-TEMPO resorcinarenes(50)(51)(52)(53) are efficient scavengers of DPPH radicals and showed superoxide dismutase-like activity.…”