TY - JOUR
T1 - 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
AU - Champciaux, Bastien
AU - Raynaud, Clément
AU - Viljoen, Albertus
AU - Chene, Loïc
AU - Thibonnet, Jérôme
AU - Vincent, Stéphane P.
AU - Kremer, Laurent
AU - Thiery, Emilie
N1 - Funding Information:
We acknowledge the French Ministry for Research and Innovation for the financial support and Dr. Frédéric Montigny (Analysis Department, Tours University) for HRMS. This study was supported by the Fondation pour la Recherche Médicale (grant DEQ20150331719 to L.K.), the Association Gregory Lemarchal and Vaincre la Mucoviscidose (grant RIF20180502320 to C.R.).
Publisher Copyright:
© 2021 Elsevier Ltd
PY - 2021/8/1
Y1 - 2021/8/1
N2 - 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.
AB - 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.
KW - Heterocycles
KW - Indoles
KW - Inhibitor
KW - Mycobacterium tuberculosis
UR - http://www.scopus.com/inward/record.url?scp=85110395361&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2021.116248
DO - 10.1016/j.bmc.2021.116248
M3 - Article
C2 - 34274760
AN - SCOPUS:85110395361
SN - 0968-0896
VL - 43
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
M1 - 116248
ER -