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

[Display omitted] 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...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2021-08, Vol.43, p.116248-116248, Article 116248
Main Authors: Champciaux, Bastien, Raynaud, Clément, Viljoen, Albertus, Chene, Loïc, Thibonnet, Jérôme, Vincent, Stéphane P., Kremer, Laurent, Thiery, Emilie
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Chemical Sciences
Dose-Response Relationship, Drug
Heterocycles
Indoles
Inhibitor
Microbial Sensitivity Tests
Molecular Structure
Mycobacterium tuberculosis
Mycobacterium tuberculosis - drug effects
Organic chemistry
Structure-Activity Relationship
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Summary:[Display omitted] 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.
ISSN:0968-0896
0960-894X
1464-3391
DOI:10.1016/j.bmc.2021.116248