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Issue 42, 2018
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Synthesis and anticholinesterase activity of 2-substituted-N-alkynylindoles

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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.

Graphical abstract: Synthesis and anticholinesterase activity of 2-substituted-N-alkynylindoles

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The article was received on 03 Sep 2018, accepted on 04 Oct 2018 and first published on 04 Oct 2018

Article type: Paper
DOI: 10.1039/C8OB02165A
Citation: Org. Biomol. Chem., 2018,16, 7926-7934

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

    T. Prochnow, A. Maroneze, D. F. Back, N. S. Jardim, C. W. Nogueira and G. Zeni, Org. Biomol. Chem., 2018, 16, 7926
    DOI: 10.1039/C8OB02165A

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