Synthesis and biological evaluation of 3,4-dihydro-1H-[1,4] oxazepino [6,5,4-hi] indol-1-ones and 4,6-dihydrooxepino [5,4,3-cd] indol-1(3H)-ones as Mycobacterium tuberculosis inhibitors.
Champciaux B, Raynaud C, Viljoen A, Chene L, Thibonnet J, Vincent SP, Kremer L, Thiery E.
This study focuses on the synthesis of 1,7- and 3,4-indole-fused lactones via a simple and efficient reaction sequence. The functionalization of these 'oxazepino-indole' and 'oxepino-indole' tricycles is carried out by palladium catalysed CC coupling, nucleophilic substitution or 1,3-dipolar cycloaddition. The evaluation of their activity against Mycobacterium tuberculosis shows that the 'oxazepino-indole' structure is a new inhibitor of M. tuberculosis growth in vitro.