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Conformational study of the cholinergic agonist pilocarpidine, isopilocarpidine, and related species

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Abstract

A conformational study on the energies and geometries of the stable conformers of the cholinergic agonist pilocarpidine and of its inactive isomer, isopilocarpidine, has been carried out by molecular mechanics MM2 and by semiempirical quantum chemical AM1. The former predicts an envelope conformation of the γ-lactone nucleus, whereas AM1 predicts a planar conformation. The relative energies of the different conformations of both isomers are strongly dependent on the relative orientation of the imidazole moiety. Other related species, intermediate steps in their synthesis, and the anion intermediate in the epimerization are also discussed.

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Authors and Affiliations

  1. Departamento de Química Orgánica, Universidad de Salamanca, Salamanca, Spain

    Francisco Bermejo

  2. Departamento de Química Física, Universidad de Valladolid, Valladolid, Spain

    María J. Rioseras

  3. Departamento de Química Física, Universidad de Salamanca, Salamanca, Spain

    Luis M. Tel

Authors
  1. Francisco Bermejo
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  2. María J. Rioseras
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  3. Luis M. Tel
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Bermejo, F., Rioseras, M.J. & Tel, L.M. Conformational study of the cholinergic agonist pilocarpidine, isopilocarpidine, and related species. Struct Chem 4, 363–366 (1993). https://doi.org/10.1007/BF00676831

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  • DOI: https://doi.org/10.1007/BF00676831

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