Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3304-3311.DOI: 10.6023/cjoc202301028 Previous Articles     Next Articles


曹瑞霞a,*(), 贾玉萍b   

  1. a 齐鲁师范学院化学与化工学院 济南 250200
    b 山东省药学科学院 济南 250101
  • 收稿日期:2023-01-31 修回日期:2023-03-15 发布日期:2023-05-23
  • 基金资助:
    山东省高校科技计划(J16LC52); 济南市“高校20条”项目(引进创新团队)(2020GXRC043); 齐鲁师范学院青年博士支持计划(QBJH19-0038)

Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin

Ruixia Caoa(), Yuping Jiab   

  1. a College of Chemistry and Chemical Engineering, Qilu Normal University, Jinan 250200
    b Shandong Academy of Pharmaceutical Sciences, Jinan 250101
  • Received:2023-01-31 Revised:2023-03-15 Published:2023-05-23
  • Contact: E-mail:
  • Supported by:
    Shandong Provincial Higher Educational Science and Technology Program(J16LC52); Jinan University and the Institute Innovation Program(2020GXRC043); Young Doctor Support Program of Qilu Normal University(QBJH19-0038)

In order to search for new structural anti-tumor drugs, a series of novel pyrrolo[2,3-d]pyrimidine derivatives containing coumarin were synthesized and evaluated for their inhibitory activities against rat glioma cell (C6), human melanoma cell (A375) and oral squamous cell (FaDu) by using methyl thiazolyl tetrazolium (MTT) assay. These chemical structures were well characterized by nuclear magnetic resonance (NMR) and high-resolution mass spectra (HRMS) spectroscopic methods. 7-[7-(2-Fluorobenzyl)-5-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-4-methylchromen-2-one (II1), 7-[7-(2-fluo- robenzyl)-5-(4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-4-methyl-chromen-2-one (II4), 7-[7-(3-fluorobenzyl)-5-(4- methoxy-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-4-methyl-chromen-2-one (III1), 7-[5-(4-chlorophenyl)-7-(3-fluoroben- zyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-4-methyl-chromen-2-one (III3) and 7-[7-(3-fluorobenzyl)-5-(4-fluorophenyl)-7H- pyrrolo[2,3-d]pyrimidin-4-yloxy]-4-methyl-chromen-2-one (III4) had better inhibitory activity against C6 cells than imatinib, compound II4 showed the most potent inhibitory activity against C6 cells with the IC50 values of 9.60 μmol/L. Compounds I2 had better inhibitory activity against FaDu cells than cisplatin, IC50 was 38.61μmol/L.

Key words: coumarin, synthesis, anticancer