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Substituent effect of ring-substituted 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides in relation to their electrochemical and biological activity
Journal of Electroanalytical Chemistry ( IF 4.1 ) Pub Date : 2021-09-01 , DOI: 10.1016/j.jelechem.2021.115667
Július Gajdár 1 , Jiří Kos 2 , Tomáš Goněc 3 , Marie Brázdová 4 , Zuzana Soldánová 4 , Miroslav Fojta 4 , Josef Jampílek 5 , Jiří Barek 1 , Jan Fischer 1
Affiliation  

Two groups of novel anti-infective agents, 3-hydroxynaphthalene-2-carboxanilides and 2-hydroxynaphthalene-1-carboxanilides, were studied by voltammetric techniques at the glassy carbon electrode in aqueous media. Oxidation of hydroxyl group was observed for all forty-four studied compounds, all of them differentiated by a position and a substituent on the benzene moiety. A shift of the oxidation potential was observed for all cases based on electron-donating or electron-withdrawing properties of substituents. These shifts were successfully correlated with Hammett σ substituent constants for meta- and para- substituted compounds. The observed differences in electrochemical behaviour (a shift of the oxidation potential of the unsubstituted compound, and the changes in the value of the reaction constant ρ) between the two studied groups were highlighted and discussed. In addition, an attempt was made to correlate the electrochemical behaviour with the previously obtained in vitro anti-infective (antibacterial, antimycobacterial, antiprotozoal) activities and herbicidal activity. Due to the moderate activity only limited conclusions could be made. However, good relationships were observed between the oxidation potential and antitrypanosomal activities.



中文翻译:

环取代的 3-羟基萘-2-甲酰苯胺和 2-羟基萘-1-甲酰苯胺对其电化学和生物活性的取代作用

两组新型抗感染剂,3-羟基萘-2-甲酰苯胺和2-羟基萘-1-甲酰苯胺,在水介质中的玻璃碳电极上通过伏安技术进行了研究。对所有 44 种研究的化合物都观察到羟基的氧化,所有这些化合物都通过苯部分的位置和取代基来区分。基于取代基的给电子或吸电子特性,在所有情况下都观察到氧化电位的变化。这些变化成功地与哈米特 σ 取代基常数相关联,用于间位对位取代的化合物。强调并讨论了两个研究组之间观察到的电化学行为差异(未取代化合物的氧化电位变化,以及反应常数 ρ 值的变化)。此外,还尝试将电化学行为与先前获得的体外抗感染(抗菌、抗分枝杆菌、抗原生动物)活性和除草活性相关联。由于活动适度,只能得出有限的结论。然而,在氧化电位和抗锥虫活性之间观察到良好的关系。

更新日期:2021-09-20
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