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

Stefanie Weyler, Younis Baqi, Petra Hillmann, Marko Kaulich, Andrea M. Hunder, Ingrid A. Müller, Christa E. Müller^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

54 Citations (Scopus)

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.

Original language	English
Pages (from-to)	223-227
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2007.10.082
Publication status	Published - Jan 1 2008
Externally published	Yes

Keywords

Antagonists
Anthraquinones
Combinatorial synthesis
P2Y receptors
Ullmann coupling reaction

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmcl.2007.10.082

Cite this

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title = "Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists",

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.",

keywords = "Antagonists, Anthraquinones, Combinatorial synthesis, P2Y receptors, Ullmann coupling reaction",

author = "Stefanie Weyler and Younis Baqi and Petra Hillmann and Marko Kaulich and Hunder, {Andrea M.} and M{\"u}ller, {Ingrid A.} and M{\"u}ller, {Christa E.}",

note = "Funding Information: This work was funded by the DFG (GRK 804) and the DAAD (scholarship for Y.B.). We thank Karen Schmeling for skilfull technical assistance. ",

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AU - Weyler, Stefanie

AU - Baqi, Younis

AU - Hillmann, Petra

AU - Kaulich, Marko

AU - Hunder, Andrea M.

AU - Müller, Ingrid A.

AU - Müller, Christa E.

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