title: Phenolic 4-hydroxy and 3,5-dihydroxy derivatives of 3-phenoxyquinoxalin-2(1H)-one as potent aldose reductase inhibitors with antioxidant activity.
abstract: A group of novel quinoxalinone derivatives (4a-h) were prepared and investigated for their inhibitory activity against ALR2 and antioxidant activity. Most of them were found to be potent aldose reductase inhibitors with IC50 values ranging from 0.019 to 0.982 μM. The most active compound 2-(3-(4-hydroxyphenoxy)-6-fluoro-2-oxoquinoxalin-1(2H)-yl)acetic acid (4c) also had an excellent selectivity. In addition, a number of compounds showed strong antioxidant activity and the phenolic 3,5-dihydroxyl compound 4f with 7-chloro in the quinoxalinone core was most active in scavenging the DPPH radical and suppressing lipid peroxidation.
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Yingang
authors.initials: Y
authors.lastname: Zou
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Xiangyu
authors.initials: X
authors.lastname: Qin
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Hao
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Shaoqi
authors.initials: S
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Yanchun
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Zhongfei
authors.initials: Z
authors.lastname: Han
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China. Electronic address: mabing@bit.edu.cn.
authors.forename: Bing
authors.initials: B
authors.lastname: Ma
authors.affiliation: Department of Applied Chemistry, Beijing Institute of Technology, No. 5, Zhongguancun South Street, 100081 Beijing, China.
authors.forename: Changjin
authors.initials: C
authors.lastname: Zhu
mesh_terms: D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000607831:3-phenoxyquinoxalin-2(1H)-one; D000975:Antioxidants; D004791:Enzyme Inhibitors; D011810:Quinoxalines; D000449:Aldehyde Reductase
keywords: Aldose reductase inhibitor; Antioxidant; Quinoxalines; Structure–activity relationships