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
Bioorganic & medicinal chemistry · 2021-06
Abstract
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.
MeSH terms
- Mycobacterium tuberculosis
- Anti-Bacterial Agents
- Microbial Sensitivity Tests
- Molecular Structure
- Structure-Activity Relationship
- Dose-Response Relationship, Drug