Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 385-393.DOI: 10.6023/cjoc201608031 Previous Articles     Next Articles



王淑霞, 高梦颖, 谭官海, 马海霞, 赵莹莹, 杜鸿源, 王总帅, 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:2016-08-31 修回日期:2016-10-08 发布日期:2016-11-03
  • 通讯作者: 陈华, 李小六;
  • 基金资助:


Effects of the Substituent at C-2 Phenyl on the N-/O-Alkylation of Quinazolin-4(3H)-one and Anti-Tumor, Antimicrobial Activities of Some Compounds

Wang Shuxia, Gao Mengying, Tan Guanhai, Ma Haixia, Zhao Yingying, Du Hongyuan, Wang Zongshuai, Chen Hua, Li Xiaoliu   

  1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002
  • Received:2016-08-31 Revised:2016-10-08 Published:2016-11-03
  • Supported by:

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

A series of quinazolin-4(3H)-one derivatives 4 and 5 possessing amino alkyl side chain were synthesized by the condensation reaction of 2-aminobenzamide with substituted benzaldehyde, followed by SN2 substitution reaction with haloalkane. The effects of the substituent at C-2 phenyl on the N-/O-alkylated reaction of quinazolin-4(3H)-one were explored. Some compounds were also evaluated for their anti proliferation activities and antimicrobial activities. The results showed that when the substituent was at orth O-position on C-2 phenyl, N-alkylation was the main reaction, while at meta- or para-positions, O-alkylation was predominant, which suggested that the steric factor played a key role on this ambident nuclophilic substitution. 4-(2-((2-(3-(Benzyloxy)phenyl)quinazolin-4-yl)oxy)ethyl)morpholine (4h) showed relatively good anti-proliferative activity against A549 tumor cells with the IC50 value of 13.20 μmol/L. 2-(2-Chlorophenyl)-3-(2-(piperidin-1-yl)ethyl)quinazolin-4(3H)-one (5aa) and 2-(3-(benzyloxy)phenyl)-4-(2-(pyrrolidin-1-yl)ethoxy)quinazoline (4hb) exhibited significant anti Esche-richia coli or Shigella castellani activities, and the inhibition rates were near 100% at the concentration of 50 μg/mL. The inhi-bition rate of compound 5aa against Alternaria alternate was 100%.

Key words: quinazolin-4-one, N-/O-alkylation, anti-tumor activity, antimicrobial activity