Synthesis of chiral pyrazolo[4,3-e][1,2,4]triazine sulfonamides with tyrosinase and urease inhibitory activity

Abstract

A new series of sulfonamide derivatives of pyrazolo[4,3-e][1,2,4]triazine with chiral amino group has been synthesized and characterized. The compounds were tested for their tyrosinase and urease inhibitory activity. Evaluation of prepared derivatives demonstrated that compounds (8b) and (8j) are most potent mushroom tyrosinase inhibitors whereas all of the obtained compounds showed higher urease inhibitory activity than the standard thiourea. The compounds (8a), (8f) and (8i) exhibited excellent enzyme inhibitory activity with IC₅₀ 0.037, 0.044 and 0.042 μM, respectively, while IC₅₀ of thiourea is 20.9 μM.

Keywords:

• Pyrazolo[4,3-e][1,2,4]triazine
• sulfonamides
• tyrosinase inhibitors
• urease inhibitors

Acknowledgements

This research was partially funded by the National Science Center, Poland (grant NN405 092340). The authors wish to acknowledge The Children’s Memorial Health Institute, Warsaw, Poland for the access to Q-TOF LC/MS; mass spectrometer purchase was supported by European POIG.02.01.00-14-059/09 project.

Disclosure statement

The authors report no conflicts of interest. The authors alone are responsible for the content and writing of this article.