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

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-fluorobenzyl)-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-fluorobenzyl)-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 mu mol/L. Compounds I-2 had better inhibitory activity against FaDu cells than cisplatin, IC50 was 38.61 mu mol/L.