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Synthesis 2017; 49(23): 5159-5166
DOI: 10.1055/s-0036-1588523
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© Georg Thieme Verlag Stuttgart · New York

Synthesis and Bioactivity of Novel N-Benzylic and N-Phenethylic Ephedrine Derivatives

Mario Ellwart
Ludwig-Maximilians-Universität München, Department Chemie und Department Pharmazie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Georg Höfner
Ludwig-Maximilians-Universität München, Department Chemie und Department Pharmazie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
,
Aaron Gerwien
Ludwig-Maximilians-Universität München, Department Chemie und Department Pharmazie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
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Klaus T. Wanner
Ludwig-Maximilians-Universität München, Department Chemie und Department Pharmazie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
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Paul Knochel  *
Ludwig-Maximilians-Universität München, Department Chemie und Department Pharmazie, Butenandtstraße 5–13, Haus F, 81377 München, Germany   Email: paul.knochel@cup.uni-muenchen.de
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Publication History

Received: 28 June 2017

Accepted: 02 July 2017

Publication Date:
23 August 2017 (online)

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Abstract

A range of N-benzylic and N-phenethylic ephedrine derivatives were prepared in a one-pot procedure starting from the two enantiomers of ephedrine using the Potier reagent, and a polyfunctional aryl- or benzylic organozinc halide. The biological activity in indatraline MS Binding Assays addressing hDAT, hNET and hSERT was determined and discussed.

Key words

organozinc halides - organomagnesium halides - iminium ion - ephedrine - binding assays

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588523.
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