Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 455-461.DOI: 10.6023/cjoc201607045 Previous Articles     Next Articles



孙佳婧, 周利凯, 谭官海, 李帅, 王淑霞, 陈华, 李小六   

  1. 河北大学化学与环境科学学院 河北省化学生物学重点实验室 保定 071002
  • 收稿日期:2016-07-29 修回日期:2016-09-13 发布日期:2016-10-09
  • 通讯作者: 陈华, 李小六;
  • 基金资助:


Synthesis and Anti-tumor Activity of Novel Quinazolin-4-one Derivatives

Sun Jiajing, Zhou Likai, Tan Guanhai, Li Shuai, Wang Shuxia, Chen Hua, Li Xiaoliu   

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002
  • Received:2016-07-29 Revised:2016-09-13 Published:2016-10-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21372060), the Hebei Provincal Natural Science Fund for Distinguished Young Scholars (Incubation) (No. B2015201005).

A series of novel C-2 and N-3 disubstituted quinazolin-4(3H)-one derivatives 5 possessing amino acid chain were synthesized by the addition reaction of imine with iminoketene and aromatization using anthranilic acid, aromatic aldehyde and glycine ethyl ester as starting materials. After elimination of carboxymethyl in the acidic condition, novel quinazolin-4(3H)-one derivatives 9 bearing amino side chain were designed and synthesized by SN2 substitution reaction. The compounds were evaluated for their anti-proliferation activities against four tumor cells. The results showed that some of the compounds, such as 9ba and 9bc showed significantly anti Hela activity with the IC50 values of 8.16 μM and 7.47 μM, respectively, while 9bc and 9bd against A549 with the IC50 values of 5.62 μM and 9.54 μM, respectively. Structure activity relationship analysis of these analogues suggested that coumarin substituent (extended π planar aromatic ring) on C-2 position and the introduction of amino side chain should be favorable to their anti-tumor activities.

Key words: quinazolin-4-one, anti-tumor activity, iminoketene, amino side chain, elimination of carboxymethyl, coumarin