Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

Younis Baqi; Christa E. Müller

doi:10.1016/j.tetlet.2012.09.011

Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

Younis Baqi^*, Christa E. Müller

^*Corresponding author for this work

Chemistry

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

14 Citations (Scopus)

Abstract

A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases.

Original language	English
Pages (from-to)	6739-6742
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2012.09.011
Publication status	Published - Dec 12 2012

Keywords

Anthraquinone
Cancer
Cardiovascular
Deamination

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2012.09.011

Cite this

@article{499fa92d9cee492ea80457f1c0489280,

title = "Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity",

abstract = "A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases.",

keywords = "Anthraquinone, Cancer, Cardiovascular, Deamination",

author = "Younis Baqi and M{\"u}ller, {Christa E.}",

note = "Funding Information: The authors thank the Deutsche Forschungsgemeinschaft (DFG, GRK804) for support. Y.B. is indebted to the DAAD for receiving a fellowship. ",

year = "2012",

month = dec,

day = "12",

doi = "10.1016/j.tetlet.2012.09.011",

language = "English",

volume = "53",

pages = "6739--6742",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "50",

}

TY - JOUR

T1 - Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

AU - Baqi, Younis

AU - Müller, Christa E.

N1 - Funding Information: The authors thank the Deutsche Forschungsgemeinschaft (DFG, GRK804) for support. Y.B. is indebted to the DAAD for receiving a fellowship.

PY - 2012/12/12

Y1 - 2012/12/12

N2 - A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases.

AB - A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases.

KW - Anthraquinone

KW - Cancer

KW - Cardiovascular

KW - Deamination

UR - http://www.scopus.com/inward/record.url?scp=84868605609&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84868605609&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2012.09.011

DO - 10.1016/j.tetlet.2012.09.011

M3 - Article

AN - SCOPUS:84868605609

SN - 0040-4039

VL - 53

SP - 6739

EP - 6742

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this