Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. / Baumann, Markus; Nome, Lina Marie; Zachariassen, Zack G.; Karlshoj, Stefanie; Fossen, Torgils; Rosenkilde, Mette M.; Vabeno, Jon; Haug, Bengt Erilc.

In: Tetrahedron, Vol. 73, No. 27-28, 2017, p. 3866-3877.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Baumann, M, Nome, LM, Zachariassen, ZG, Karlshoj, S, Fossen, T, Rosenkilde, MM, Vabeno, J & Haug, BE 2017, 'Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism', Tetrahedron, vol. 73, no. 27-28, pp. 3866-3877. https://doi.org/10.1016/j.tet.2017.05.057

APA

Baumann, M., Nome, L. M., Zachariassen, Z. G., Karlshoj, S., Fossen, T., Rosenkilde, M. M., Vabeno, J., & Haug, B. E. (2017). Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron, 73(27-28), 3866-3877. https://doi.org/10.1016/j.tet.2017.05.057

Vancouver

Baumann M, Nome LM, Zachariassen ZG, Karlshoj S, Fossen T, Rosenkilde MM et al. Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. Tetrahedron. 2017;73(27-28):3866-3877. https://doi.org/10.1016/j.tet.2017.05.057

Author

Baumann, Markus ; Nome, Lina Marie ; Zachariassen, Zack G. ; Karlshoj, Stefanie ; Fossen, Torgils ; Rosenkilde, Mette M. ; Vabeno, Jon ; Haug, Bengt Erilc. / Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism. In: Tetrahedron. 2017 ; Vol. 73, No. 27-28. pp. 3866-3877.

Bibtex

@article{618df0e515cb41b08bba4a4638400695,
title = "Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism",
abstract = "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 α,β-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 R1 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.",
keywords = "Tripeptidomimetic, Scaffold, CXCR4 antagonist",
author = "Markus Baumann and Nome, {Lina Marie} and Zachariassen, {Zack G.} and Stefanie Karlshoj and Torgils Fossen and Rosenkilde, {Mette M.} and Jon Vabeno and Haug, {Bengt Erilc}",
year = "2017",
doi = "10.1016/j.tet.2017.05.057",
language = "English",
volume = "73",
pages = "3866--3877",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Pergamon Press",
number = "27-28",

}

RIS

TY - JOUR

T1 - Synthesis of a novel tripeptidomimetic scaffold and biological evaluation for CXC chemokine receptor 4 (CXCR4) antagonism

AU - Baumann, Markus

AU - Nome, Lina Marie

AU - Zachariassen, Zack G.

AU - Karlshoj, Stefanie

AU - Fossen, Torgils

AU - Rosenkilde, Mette M.

AU - Vabeno, Jon

AU - Haug, Bengt Erilc

PY - 2017

Y1 - 2017

N2 - 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 α,β-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 R1 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.

AB - 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 α,β-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 R1 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.

KW - Tripeptidomimetic

KW - Scaffold

KW - CXCR4 antagonist

U2 - 10.1016/j.tet.2017.05.057

DO - 10.1016/j.tet.2017.05.057

M3 - Journal article

VL - 73

SP - 3866

EP - 3877

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 27-28

ER -

ID: 182486284