Synthesis and anticholinesterase activity of 2-substituted-N-alkynylindoles

In this paper, we report a protocol for the preparation of 2-substituted-N-alkynylindoles via metalation of N-alkynylindoles followed by the capture of a 2-indolyl lithium intermediate with different electrophiles. The reactivity of the indoles prepared was also demonstrated through the reaction wit...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-10, Vol.16 (42), p.7926-7934
Main Authors: Prochnow, Thaís, Maroneze, Adriano, Back, Davi F, Jardim, Natalia S, Nogueira, Cristina W, Zeni, Gilson
Format: Article
Language:English
Subjects:
Cholinesterase
Cholinesterase inhibitors
Crystallography
Donepezil
Indoles
Intermetallic compounds
Lithium
Substitutes
Tellurides
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Summary:In this paper, we report a protocol for the preparation of 2-substituted-N-alkynylindoles via metalation of N-alkynylindoles followed by the capture of a 2-indolyl lithium intermediate with different electrophiles. The reactivity of the indoles prepared was also demonstrated through the reaction with CBr4/Ph3P for the preparation of 2-gem-dibromovinyl N-alkynylindoles and the hydrotelluration reaction of N-alkynylindoles, which led to vinylic tellurides. Some compounds prepared showed AChE inhibitory potential in the low micromolar range similar to that obtained with donepezil, a commercially available cholinesterase inhibitor.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob02165a