Synthesis of 8-phenyl substituted 3-benzazecines with allene moiety, their thermal rearrangement and evaluation as acetylcholinesterase inhibitors


Various 4′-R-substituted phenyl azacyclic allenes were synthesized in good yields, and their thermal transformations were studied. For the first time, the obtained rearrangement products—new N-bridged cyclopenta[a]indenes, and the corresponding parent allenes were evaluated as potential inhibitors of acetyl- and butyrylcholinesterase. Among the tested compounds, the allene derivative 2g proved to competitively inhibit human AChE with inhibition constant value (Ki) in the low micromolar range.

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The publication has been prepared with support of the Russian Science Foundation (project No. 18-73-10057).

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Correspondence to Alexander A. Titov.

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Kobzev, M.S., Titov, A.A., Alexandrova, E.V. et al. Synthesis of 8-phenyl substituted 3-benzazecines with allene moiety, their thermal rearrangement and evaluation as acetylcholinesterase inhibitors. Mol Divers (2021).

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  • Azacyclic allenes
  • Acetylcholinesterase inhibitors
  • N-bridged cyclopenta[a]indenes