Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists

Stefanie Weyler; Younis Baqi; Petra Hillmann; Marko Kaulich; Andrea M Hunder; Ingrid A Müller; Christa E Müller

doi:10.1016/j.bmcl.2007.10.082

Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists

Bioorg Med Chem Lett. 2008 Jan 1;18(1):223-7. doi: 10.1016/j.bmcl.2007.10.082. Epub 2007 Oct 30.

Authors

Stefanie Weyler¹, Younis Baqi, Petra Hillmann, Marko Kaulich, Andrea M Hunder, Ingrid A Müller, Christa E Müller

Affiliation

¹ Pharmaceutical Institute, Pharmaceutical Sciences Bonn, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany.

PMID: 18006312
DOI: 10.1016/j.bmcl.2007.10.082

Abstract

A library of anilinoanthraquinone derivatives was synthesized by parallel Ullmann coupling reaction of bromaminic acid with aniline derivatives in solution using a compact parallel synthesizer. The products were purified by HPLC and evaluated as antagonists at mouse and human P2Y2 receptors. 4-Phenylamino-substituted 1-amino-2-sulfoanthraquinones, for example, 1-amino-4-(2-methoxyphenyl)-2-sulfoanthraquinone (PSB-716), were potent P2Y2 antagonists with IC50 values in the low micromolar range.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aniline Compounds / chemical synthesis*
Aniline Compounds / pharmacology*
Animals
Anthraquinones / chemical synthesis*
Anthraquinones / pharmacology*
Combinatorial Chemistry Techniques
Humans
Inhibitory Concentration 50
Kinetics
Mice
Purinergic P2 Receptor Antagonists*
Receptors, Purinergic P2Y2
Structure-Activity Relationship

Substances

Aniline Compounds
Anthraquinones
P2RY2 protein, human
P2ry2 protein, mouse
Purinergic P2 Receptor Antagonists
Receptors, Purinergic P2Y2