Synthesis and Free Radical Scavenging Activity of Coumarin Derivatives Containing a 2-Methylbenzothiazoline Motif

被引:69
作者
Khoobi, Mehdi [2 ]
Emami, Saeed [3 ,4 ]
Dehghan, Gholamreza [5 ]
Foroumadi, Alireza [1 ,6 ]
Ramazani, Ali [2 ]
Shafiee, Abbas [1 ]
机构
[1] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm & Pharmaceut Sci, Res Ctr, Tehran 14176, Iran
[2] Zanjan Univ, Dept Chem, Zanjan, Iran
[3] Mazandaran Univ Med Sci, Dept Med Chem, Sari, Iran
[4] Mazandaran Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Sari, Iran
[5] Univ Tabriz, Fac Nat Sci, Dept Biol, Tabriz, Iran
[6] Univ Tehran Med Sci, Drug Design & Dev Res Ctr, Tehran 14176, Iran
基金
美国国家科学基金会;
关键词
ABTS; Antioxidants; Benzothiazoline; Coumarin; DPPH; Radical scavenging activity; ANTIOXIDANT;
D O I
10.1002/ardp.201000271
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Coumarin and benzothiazole scaffolds can be found in a number of natural or synthetic antioxidants. In an effort to develop a novel radical scavenger and potential antioxidant, a series of coumarin derivatives containing 2-methylbenzothiazoline motif and related compounds was synthesized and evaluated for their DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS(center dot+) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radicals scavenging activities. Among them, 7-hydroxy-3-(2-methyl-2,3-dihydrobenzo[d]-thiazol-2-yl)-2H-chromen-2-one (3e) has shown a significant free radical scavenging activity. From the structure-activity point of view, it was found that phenolic coumarin ring and benzothiazoline moiety in target compounds may contribute to the scavenging activity against free radicals.
引用
收藏
页码:588 / 594
页数:7
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