Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors

3-Formylchromone (1), 3-methyl-7-hydroxychromone (2) and Schiff bases of 3-formylchromone 3–19 have been synthesized and their anti-thymidine phosphorylase inhibitory activity was evaluated. Compounds 1–19 showed a varying degree of thymidine phosphorylase inhibition with IC50 values 19.77 ± 3.25 to 480.21 ± 2.34 μM. Their activity was compared with the standard 7-deazaxanthine (IC50 = 39.28 ± 0.76 μM). Compound 12 showed an excellent thymidine phosphorylase inhibitory activity with an IC50 value of 19.77 ± 3.25 μM, better than the standard. Compound 4 also showed an excellent inhibitory activity (IC50 = 40.29 ± 4.56 μM). The parent 3-formylchromone (1) and 3-methyl-7-hydroxychromone (2) were found to be inactive. The structures of the compounds were elucidated by using spectroscopic techniques, including 1H NMR, EI MS, IR, UV and elemental analysis.

A series of substituted Schiff bases of 3-formylchromone have been synthesized and screened against thymidine phosphorylase enzyme. Results were astounding and several leads were obtained for further optimization.Figure optionsDownload as PowerPoint slide