Synthesis of phenazines and lactone and halogenated derivatives

This paper reports on the preparation, chemical reactivity, and activity against Mycobacterium tuberculosis of phenazines derived from the natural naphthoquinones beta-lapachone and lausone. The phenazines were converted into macrolactone compounds through reactions with peracetic acid, m-chlorobenzoic acid, and ozone. Reactions with trichloroisocyanuric acid were performed, in which two phenazines were converted into -chloroacetals and the phenazine derived from beta-lapachone was converted into another phenazine by the action of N-bromosuccinimide. In total, nine compounds previously unreported in the literature were synthesized, and three others, already described, were prepared by other methods with higher yields. Twelve compounds prepared in this work, including both new and previously described compounds, were tested against Mycobacterium tuberculosis, of which three show potential for the development of new therapeutic alternatives for tuberculosis.

Autorentext

Pharmacist from the Federal University of Rio de Janeiro and master's and doctorate in Natural Product Chemistry, in the area of organic synthesis, from the Federal University of Rio de Janeiro, Professor of Organic Chemistry at the Federal Institute of Education, Science, and Technology of Rio de Janeiro.