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 microg per mL on Mycocabteriumtuberculosis H37Rv. These results justify further research into its value as a potential lead for an original treatment of tuberculosis.
Silva
Raphael S F
RS
Núcleo de Pesquisas de Produtos Naturais, CCS, Universidade Federal do Rio de Janeiro, Ilha do Fundão, 21941-902 Rio de Janeiro, RJ, Brazil.
Pinto
Maria do Carmo F R
Mdo C
Goulart
Marília O F
MO
de Souza Filho
José D
JD
Neves
Ivan
I
Lourenço
Maria Cristina S
MC
Pinto
Antonio V
AV
D000995:Antitubercular Agents / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D010084:Oxidation-Reduction; D010619:Phenazines / Q000737:chemistry*; D011810:Quinoxalines; D013329:Structure-Activity Relationship
D000995:Antitubercular Agents; D007783:Lactones; D010619:Phenazines; D011810:Quinoxalines