Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2445-2453.DOI: 10.6023/cjoc202011013 Previous Articles     Next Articles



张晓平a,*(), 金桂勇a, 陈芝飞b, 王清福b, 赵森森b, 武志勇a, 万帅b, 席高磊b,*(), 赵旭b,*()   

  1. a 河南农业大学烟草学院 郑州 450002
    b 河南中烟工业有限责任公司技术中心 郑州 450000
  • 收稿日期:2020-11-09 修回日期:2021-01-11 发布日期:2021-02-22
  • 通讯作者: 张晓平, 席高磊, 赵旭
  • 基金资助:

Synthesis and Antioxidant Properties of Pyrazine-Thiazole Bi-heteroaryl Compounds

Xiaoping Zhanga(), Guiyong Jina, Zhifei Chenb, Qingfu Wangb, Sensen Zhaob, Zhiyong Wua, Shuai Wanb, Gaolei Xib(), Xu Zhaob()   

  1. a College of Tobacco Science, Henan Agricultural University, Zhengzhou 450002
    b Technology Center, China Tobacco Henan Industrial Co., Ltd., Zhengzhou 450000
  • Received:2020-11-09 Revised:2021-01-11 Published:2021-02-22
  • Contact: Xiaoping Zhang, Gaolei Xi, Xu Zhao
  • Supported by:
    Young Talents Program of Henan Agricultural University(30500602)

In order to find novel pyrazine- and thiazole-based derivatives with potent antioxidant properties, eight pyrazine-thiazole bi-heteroaryl compounds were designed and prepared via active group splicing method between pyrazine-N- oxides and thiazoles. They were structurally characterized by 1H NMR, 13C NMR, IR, and HPLC-MS. Antioxidant abilities of the obtained compounds were evaluated by inhibiting radicals induced oxidation of DNA and quenching radicals. The results showed that eight compounds can effectively inhibit radicals induced oxidation of DNA and quench radicals, which revealed that the compounds have strong radical scavenging properties and reduction ability, and can be potential antioxidants. The effective measurement factor (n) values of these compounds ranged from 1.48 to 2.12 in 2,2-azobis(2-amidinopropanehydro- chloride) (AAPH) induced oxidation of DNA. The absorbance percentages of eight compounds to the blank thiobarbituric acid reactive substance (TBARS percentage) were 54.3%~76.1% and 55.4%~68.3% in inhibiting HO• and glutathione radical (GS•) induced oxidation of DNA, respectively. Eight compounds can scavenge 2,2-azinobis(3-ethylbenzothiazoline-6-sul- fonate) cationic radical (ABTS•) and 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•). In addition, it was found that the antioxidant activity of pyrazine-thiazole bi-heteroaryl compounds was significantly higher than that of pyrazine-oxazole bi-heteroaryl compound.

Key words: pyrazine-thiazole, oxidative cross-dehydrogenative coupling, antioxidant, DNA, free radical