Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles

Q3 Pharmacology, Toxicology and Pharmaceutics
A. Spasov, A. A. Brigadirova, O. Zhukovskaya, A. S. Morkovnik, Yuliya V. Lifanova
{"title":"Search for compounds with antioxidant and antiradical activity among N9-substituted 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles","authors":"A. Spasov, A. A. Brigadirova, O. Zhukovskaya, A. S. Morkovnik, Yuliya V. Lifanova","doi":"10.3897/rrpharmacology.8.85498","DOIUrl":null,"url":null,"abstract":"Introduction: Biphenyl and imidazobenzimidazole derivatives attract ongoing attention as a combination of these two privileged substructures with promising pharmacological activities. The aim of this study was to synthesize and investigate in vitro antioxidant activity of promising novel compounds: 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles.\n Materials and methods: The newly synthesized compounds were characterized by IR, 1H NMR and CHBr(Cl)NO analyses. All newly synthesized compounds were screened for their in vitro antioxidant activity: inhibition of lipid peroxidation (LPO), 2,2’-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) radical cation decolorization and inhibition of hemoglobin (Hb)-H2O2-induced luminol chemiluminescence.\n Results and discussion: 2-Amino-3-[(2-biphenyl-4-yl)-2-oxo-ethyl)]-1-R-1Н-benzimidazolium bromides were synthesized, and their cyclization into functionalized imidazo[1,2-a]benzimidazole derivatives was studied. The resulting compounds showed LPO inhibitory activity comparable to that of dibunol. Compounds 1a and 1d (see graphical abstract), containing a methyl or dimethylaminoethyl substituent in the N9 position also proved to be equally highly active in the Hb-H2O2-induced luminol chemiluminescence model, while compound 1a was somewhat more active than 1d in the ABTS• radical scavenging assay.\n Conclusion: The study showed that compounds 1a and 1d have the highest antioxidant activity. Thus, this new class of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazole derivatives represents a valuable leading series with great potential for use as antioxidants and as promising candidates for further efficacy evaluation.\n Graphical abstract:\n \n \n","PeriodicalId":21030,"journal":{"name":"Research Results in Pharmacology","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2022-08-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Research Results in Pharmacology","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3897/rrpharmacology.8.85498","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
引用次数: 0

Abstract

Introduction: Biphenyl and imidazobenzimidazole derivatives attract ongoing attention as a combination of these two privileged substructures with promising pharmacological activities. The aim of this study was to synthesize and investigate in vitro antioxidant activity of promising novel compounds: 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazoles. Materials and methods: The newly synthesized compounds were characterized by IR, 1H NMR and CHBr(Cl)NO analyses. All newly synthesized compounds were screened for their in vitro antioxidant activity: inhibition of lipid peroxidation (LPO), 2,2’-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS•+) radical cation decolorization and inhibition of hemoglobin (Hb)-H2O2-induced luminol chemiluminescence. Results and discussion: 2-Amino-3-[(2-biphenyl-4-yl)-2-oxo-ethyl)]-1-R-1Н-benzimidazolium bromides were synthesized, and their cyclization into functionalized imidazo[1,2-a]benzimidazole derivatives was studied. The resulting compounds showed LPO inhibitory activity comparable to that of dibunol. Compounds 1a and 1d (see graphical abstract), containing a methyl or dimethylaminoethyl substituent in the N9 position also proved to be equally highly active in the Hb-H2O2-induced luminol chemiluminescence model, while compound 1a was somewhat more active than 1d in the ABTS• radical scavenging assay. Conclusion: The study showed that compounds 1a and 1d have the highest antioxidant activity. Thus, this new class of 2-(biphenyl-4-yl)imidazo[1,2-a]benzimidazole derivatives represents a valuable leading series with great potential for use as antioxidants and as promising candidates for further efficacy evaluation. Graphical abstract:
在N9取代的2-(联苯-4-基)咪唑并[1,2-a]苯并咪唑中寻找具有抗氧化和抗自由基活性的化合物
引言:联苯和咪唑并苯并咪唑衍生物作为这两种具有良好药理活性的特殊亚结构的组合,引起了人们的广泛关注。本研究的目的是合成并研究有前景的新化合物:2-(联苯-4-基)咪唑并[1,2-a]苯并咪唑的体外抗氧化活性。材料与方法:用红外光谱、核磁共振氢谱和CHBr(Cl)NO分析对新合成的化合物进行了表征。筛选了所有新合成的化合物的体外抗氧化活性:抑制脂质过氧化(LPO)、2,2'-叠氮基双-(3-乙基苯并噻唑啉-6-磺酸)(ABTS•+)自由基阳离子脱色和抑制血红蛋白(Hb)-H2O2诱导的鲁米诺化学发光。结果与讨论:合成了2-氨基-3-[(2-联苯-4-基)-2-氧代乙基)]-1-R-1Н-苯并咪唑鎓溴化物,并研究了它们环化为功能化咪唑并[1,2-a]苯并咪唑衍生物的反应。所得化合物显示出与二丁醇相当的LPO抑制活性。在N9位含有甲基或二甲基氨基乙基取代基的化合物1a和1d(见图形摘要)在Hb-H2O2诱导的鲁米诺化学发光模型中也被证明具有同样高的活性,而在ABTS•自由基清除测定中,化合物1a的活性略高于1d。结论:化合物1a和1d具有最高的抗氧化活性。因此,这类新的2-(联苯-4-基)咪唑并[1,2-a]苯并咪唑衍生物代表了一个有价值的领先系列,具有用作抗氧化剂的巨大潜力,也是进一步疗效评估的有前途的候选者。图形摘要:
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Research Results in Pharmacology
Research Results in Pharmacology Medicine-Pharmacology (medical)
CiteScore
1.50
自引率
0.00%
发文量
32
审稿时长
12 weeks
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信