4.7 Article

Design and Synthesis of Backbone-Fused, Conformationally Constrained Morpholine-Proline Chimeras

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 6, Pages 4237-4247

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03413

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Funding

  1. NSERC
  2. Servier

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We report the synthesis of two novel bridged morpholine-proline chimeras 4 and 5, which represent rigid conformationally locked three-dimensional structures wherein the lone pairs of electrons on oxygen and nitrogen are oriented in spatially different east-west and north-west directions, respectively. In combination with the presence of a carboxylic acid, the electronic features of these compounds may be useful in the context of peptidomimetic design of biologically relevant compounds. Quantitative estimates of the basicity of the nitrogen atoms were obtained using conceptual density functional theory analysis.

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