Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2616-2624.DOI: 10.6023/cjoc201901053 Previous Articles     Next Articles



张强健a, 王芸芸a, 赵雨珣a, 马崇慧a, 徐徐a,c, 谷文a,c, 杨益琴b,c, 王石发a,c   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 南京林业大学轻工与食品学院 南京 210037;
    c 南京林业大学林业资源高效加工利用协同创新中心 南京 210037
  • 收稿日期:2019-01-30 修回日期:2019-03-17 发布日期:2019-04-11
  • 通讯作者: 王石发
  • 基金资助:


Design, Synthesis and Antioxidant Application of Camphorsulfonic Acid Thiazolylhydrazone Derivatives

Zhang Qiangjiana, Wang Yunyuna, Zhao Yuxuna, Ma Chonghuia, Xu Xua,c, Gu Wena,c, Yang Yiqingb,c, Wang Shifaa,c   

  1. a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b College of Light Industry and Food, Nanjing Forestry University, Nanjing 210037;
    c Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037
  • Received:2019-01-30 Revised:2019-03-17 Published:2019-04-11
  • Contact: 10.6023/cjoc201901053
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31470592).

A series of camphorsulfonic acid thiazolylhydrazone derivatives were synthesized by using camphorsulfonic acid derivated from natural camphor as the starting material in three steps, including condensation with aminothiourea and cyclization with bromoacetophenone. Their structures were characterized by 1H NMR, 13C NMR and HR-MS, and their antioxidant activities were also investigated. The results showed that these compounds had good antioxidant activities compared with the positive control trolox. Among of them, (2-(2-(4-(4-cyanophenyl)thiazol-2-yl)indenyl)-7,7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q19) exhibited the relatively strong 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with IC50 value of 176 μmol/L, (2-(2-(4-(4-fluorophenyl)thiazol-2-yl)hydrazino)-7,7-dimethylbicyclo-[2.2.1]hept-1-yl)methanesulfonic acid (Q3) exhibited the relatively strong diammonium 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) radical scavenging activity with IC50 value of 20.6 μmol/L, (E)-(7,7-dimethyl-2-(2-(4-(3-methyl)-thiazol-2-yl)indenyl)bicyclo[2.2.1]hept-1-yl)-sulfonic acid (Q8) exhibited the strong hydroxyl radical scavenging activity with scavenge rate 66.2%, (2-(2-(4-(4-biphenyl)thiazol-2-yl)indenyl)-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methane-sulfonic acid (Q20) exhibited the relatively strong superoxide radical scavenging activity with IC50 value of 20.7 μmol/L. Compared with the positive control kojic acid, (2-(2-(4-(2-hydroxyphenyl)thiazol-2-yl)arylene)-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonic acid (Q16) exhibited remarkable tyrosinase inhibitory activity with IC50 value of 154.9 μmol/L. It was known from the structure-activity relationship that the structure of R gave great influence on the activities of thiazolylhydrazone derivatives.

Key words: camphorsulfonic acid, thiazolylhydrazone, antioxidant activity