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 Fe3+ reducing power was lower compared to both
standards carvedilol and atenolol. The study discussed structure–antioxidant
properties relationships considering electronic, steric and lipophilic
features.
Keywords: Substituted
phenylcarbamates; N-arylpiperazines; antioxidant properties; ABTS•+; FRAP;
electronic features; lipophilicity
Author: Ivan Malík, Lukáš
Stanzel, Jozef Csöllei, Jana Čurillová
Journal Code: jpfarmasigg170010
