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Synthesis 2011(17): 2848-2858  
DOI: 10.1055/s-0030-1260165
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Structure of Fluorescent Chelate Boron Complexes of 4-Anilinomethylidene-1-benzazepine-2,5-dione Ligands

Nadine Tollea, Ute Dunkela, Luciano Oehningera, Ingo Otta, Lutz Preua, Tobias Haaseb, Soenke Behrendsb, Peter G. Jonesc, Frank Totzked, Christoph Schächteled, Michael H. G. Kubbutatd, Conrad Kunick*a
a Institut für Medizinische und Pharmazeutische Chemie, Technische Universität Braunschweig, Beethovenstr. 55, 38106 Braunschweig, Germany
Fax: +49(531)3912799; e-Mail: c.kunick@tu-braunschweig.de;
b Institut für Pharmakologie, Toxikologie und Klinische Pharmazie, Technische Universität Braunschweig, Mendelssohnstr. 1, 38106 Braunschweig, Germany
c Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
d ProQinase GmbH, Breisacher Str. 117, 79106 Freiburg, Germany
Further Information

Publication History

Received 7 April 2011
Publication Date:
08 August 2011 (online)

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Synthesis and Structure of Fluorescent Chelate Boron Complexes of 4-Anilinomethylidene-1-benzazepine-2,5-dione LigandsSynthesis 2011; 2011(19): 3208-3208
DOI: 10.1055/s-0030-1260205

Abstract

As analogues to the paullone kinase inhibitor family, boron chelate complexes of 4-anilinomethylidene-1-benzazepine-2,5-diones were prepared by reacting the ligands with boron trifluoride etherate or triphenylborane. The structures of the novel heterocyclic ring systems were established by X-ray structure analysis of two representative derivatives. The stability of the compounds in dimethylsulfoxide solution is dependent on the electronic properties of the aryl ring substituents. The fluorescent properties of the molecules are suitable for imaging the intracellular compound distribution by confocal laser microscopy.

Key words

boron - chelates - lactams - ligands - spectroscopy

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