A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis

We report here an alternative to the MCPBA or ozonolysis-based oxidation methods of quinoxaline-featuring compounds prepared from beta-lapachones. The use of peracetic acid allowed a simple preparation of the corresponding macrolactones by cleavage of the ring system. These lactones were evaluated for their antimycobacterial potential and compound 4 turned out to have an MIC of 0.62 μg per mL on Mycocabteriumtuberculosis H37Rv. These results justify further research into its value as a potential lead for an original treatment of tuberculosis.

Graphical abstractA macrolactone derived from β-lapachone phenazine has shown high activity against Mycobacterium tuberculosis and it is presented as an alternative method for preparation of lactones from benzo[a]phenazines. Figure optionsDownload full-size imageDownload as PowerPoint slide