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

Bastien Champciaux, Clément Raynaud, Albertus Viljoen, Loïc Chene, Jérôme Thibonnet, Stéphane P. Vincent, Laurent Kremer, Emilie Thiery

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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 C[sbnd]C 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.

Original languageEnglish
Article number116248
JournalBioorganic and Medicinal Chemistry
Volume43
DOIs
Publication statusPublished - 1 Aug 2021

Keywords

  • Heterocycles
  • Indoles
  • Inhibitor
  • Mycobacterium tuberculosis

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