The in Vitro Antioxidant Properties of 2-Alkoxyphenylcarbamic Acid Derivatives Containing a 4´-(Substituted Phenyl)piperazin-1´-Yl Moiety Determined by the 2,2´-Azinobis(3-Ethylbenzothiazoline-6-Sulfonic Acid) Derived Radical Cation (Abts•+) and Ferric Re

Abstract

In an effort to comprehensively characterize an antioxidant profile of 2-alkoxyphenylcarbamic acid-based compounds containing a 4´-(substituted phenyl)piperazin-1´-yl fragment, they were in vitro screened in the 2,2´-azino-bis(3-ethylbenzothiazoline-6--sulfonic acid) derived radical cation (ABTS •+ ) and ferric reducing antioxidant power (FRAP) assay using the UV/VIS spectrophotometry. The ABTS•+ scavenging (reducing) potential of 1-[3-(2-methoxyphenylcarbamoyl)oxy-2-hydroxypropyl]-4-(4--fluorophenyl)piperazin-1-ium chloride was found to be the most promising and it was comparable to the efficiency of the carvedilol reference drug. Moreover, that 4´-fluoro group-containing compound was regarded as more active than the atenolol standard. When testing the molecules´ power to reduce the ferric 2,4,6-tris (2-pyridyl)-s-triazine complex [Fe(III)(TPTZ) 2 ] 3+ , the most prospective was 1-[3-(2-ethoxyphenylcarbamoyl)oxy-2--hydroxypropyl]-4-(4-fluorophenyl)piperazin-1-ium chloride. On the other hand, its Fe 3+ reducing power was lower compared to both standards carvedilol and atenolol. The study discussed structure-antioxidant properties relationships considering electronic, steric and lipophilic features.

Synthesis, antioxidant activity, and HPLC enantioseparation of aryloxyaminopropanols derived from naphthalen-2-ol

“…The antioxidant activity relates to the activity of the standard substance trolox, whose activity was determined simultaneously with the samples measured. The method is dependent on pH, hence buffers containing disodium hydrogen phosphate and potassium dihydrogen phosphate were used for the measurement (Re et al, 1999;Malík et al, 2017).…”

Synthesis and High Antioxidant Activity of C-Alkyl Calix[4]resorcinarene and C-Alkyl Calix[4]pyrogallolarene Derivatives

“…Because of that, the researchers' attention is gradually shifted to synthetic antioxidant agents. Synthetic antioxidant agents are mainly designed and prepared based on aromatic compounds (Malik et al, 2017). Chalcone derivative with 3,4-methylenedioxy functional group gave the IC50 value of 159 µg mL -1 (Venkatachalam et al, 2012).…”