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Synthesis 2021; 53(20): 3735-3743
DOI: 10.1055/a-1517-7177
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Protecting-Group-Free Synthesis of GB1107: An Orally Active Galectin-3 Antagonist

Jacob St-Gelais
,
Denis Giguère∗
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), PROTEO, and Université Laval.
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Abstract

Small-molecule galectin inhibitors are useful research tools that could also be used as potential drug candidates. In that context, GB1107, a monosaccharidic galectin inhibitor, was shown to be an orally active galectin-3 antagonist that inhibits lung adenocarcinoma growth. Herein, a protecting-group-free synthesis of GB1107, along with other analogues is described. Starting from inexpensive levoglucosan, a Payne rearrangement/azidation process was used as key step. Finally, the use of a log P determination method based on 19F NMR spectroscopy was explored to assess the lipophilicity of galectin inhibitors.

Key words

synthetic inhibitors - galectins - GB1107 - TD139 - lipophilicity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1517-7177.
  • Supporting Information


Publication History

Received: 24 March 2021

Accepted after revision: 26 May 2021

Accepted Manuscript online:
26 May 2021

Article published online:
27 July 2021

© 2021. Thieme. All rights reserved

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