Journal
TETRAHEDRON
Volume 73, Issue 27-28, Pages 3866-3877Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.05.057
Keywords
Tripeptidomimetic; Scaffold; CXCR4 antagonist
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Funding
- Research Council of Norway through the Norwegian NMR Platform, NNP [226244/F50]
- University of Bergen
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We here report the preparation of a new 2,6,8-trisubstituted bicyclic tripeptidomimetic scaffold through TFA-mediated cyclization of a linear precursor containing three side chains. The introduction of a triphenylmethyl-protected thiol into carboxylic acid containing building blocks through sulfa Michael additions onto alpha,beta-unsaturated hexafluoroisopropyl esters is described. The stereoselectivity of the bicycle formation was found to be somewhat lower than that previously reported for analogous 3,6,8-trisubstituted scaffolds. Moreover, the configuration of the linear precursor directs the stereochemical outcome of the cyclization differently when the R-1 side chain is positioned on C2 in the bicycles (present work) instead of C3 (previous work). Tripeptidomimetic compounds based on the new scaffold were synthesized and evaluated for antagonistic potency toward CXCR4, and one compound (45a) displayed similar activity to earlier reported 3,6,8-tripeptidomimetic bicycles. (C) 2017 Elsevier Ltd. All rights reserved.
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