75313-54-1Relevant academic research and scientific papers
Ullmann reactions of 1-amino-4-bromoanthraquinones bearing various 2-substituents furnishing novel dyes
Malik, Enas M.,Rashed, Mahmoud,Wingen, Lukas,Baqi, Younis,Müller, Christa E.
, p. 33 - 40 (2016/04/20)
Novel 1-amino-4-(ar)alkylaminoanthraquinone derivatives bearing different substituents (Br, CH2OH, CN, or CH3) at the 2-position of the anthraquinone scaffold were synthesized by copper-catalyzed Ullmann condensation. The 2-substituted 1-amino-4-bromoanthraquinone derivatives (bromaminic acid analogues) were reacted with a variety of alkyl-, aryl-, and aralkylamines. Different reaction conditions were applied depending on the physical state of the amine and the nature of the substituent at the 2-position of the anthraquinone scaffold. A solvent-free synthetic procedure was developed for reactions with liquid amines. Condensation with solid amines required the addition of a solvent, and reaction conditions had to be optimized for each of the anthraquinone derivatives. Our results emphasize that copper-catalyzed reactions are highly variable depending on the molecules and anions present in the medium, since different reaction mechanisms apply. The synthesized anthraquinone derivatives may be useful as new dyes, or may show biological activity and could be employed as tool compounds in experimental pharmacology.
Discovery of potent competitive antagonists and positive modulators of the P2X2 receptor
Baqi, Younis,Hausmann, Ralf,Rosefort, Christiane,Rettinger, Jürgen,Schmalzing, Günther,Müller, Christa E.
experimental part, p. 817 - 830 (2011/04/15)
Evaluation and optimization of anthraquinone derivatives related to Reactive Blue 2 at P2X2 receptors yielded the first potent and selective P2X2 receptor antagonists. The compounds were tested for inhibition of ATP (10 μM) mediated currents in Xenopus oocytes expressing the rat P2X2 receptor. The most potent antagonists were sodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2- ylamino)phenylamino]- 9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (63, PSB-10211, IC50 8 6 nM) and disodium 1-amino- 4-[3-(4,6-dichloro[1,3, 5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene- 2-sulfonate (57, PSB-1011, IC50 79 nM). Compound 57 exhibited a competitive mechanism of action (pA2 7.49). It was >100-fold selective versus P2X4, P2X7, and several investigated P2Y receptor subtypes (P2Y24612); selectivity versus P2X1 and P2X3 receptors was moderate (>5-fold). Compound 57 was >13-fold more potent at the homomeric P2X2 than at the heteromeric P2X2/3 receptor. Several anthraquinone derivatives were found to act as positive modulators of ATP effects at P2X2 receptors, for example, sodium 1-amino-4-(3-phenoxyphenylamino)-9,10-dioxo-9,10- dihydroanthracene-2-sulfonate (51, PSB-10129, EC50 489 nM), which led to about a 3-fold increase in the ATP-elicited current.
Development of potent and selective inhibitors of ecto-5′- nucleotidase based on an anthraquinone scaffold
Baqi, Younis,Lee, Sang-Yong,Iqbal, Jamshed,Ripphausen, Peter,Lehr, Anne,Scheiff, Anja B.,Zimmennann, Herbert,Bajorath, Jürgen,Müller, Christa E.
experimental part, p. 2076 - 2086 (2010/08/19)
ecto-5′-Nucleotidase (eN, CD73) plays a major role in controlling extracellular adenosine levels. eN inhibitors have potential as novel drugs, for example, for the treatment of cancer. In the present study, we synthesized and investigated a series of 55 anthraquinone derivatives as potential inhibitors of eN, 11 of which are novel compounds and another 11 of which had previously been described but have now been synthesized by an improved method. We identified several potent inhibitors of rat eN. The most potent compounds were l-amino-4-[4-fluoro-2-carboxyphenylamino]-9,10-dioxo-9,10-dihydroanthracene-2- sulfonate (45, PSB-0952, K1 = 260 nM) and 1-amino-4-[2- anthracenylamino]-9,10-dioxo-9,10dihydroanthracene-2-sulfonate (52, PSB-0963, 150 nM), with 52 being the most potent eN inhibitor described to date. Selected compounds were further characterized and found to exhibit a competitive mechanism of inhibition. Investigations of ecio-nucleoside triphosphate diphosphohydrolases (NTPDases) and the P2Y receptor subtypes P2Y2, P2Y4, P2Y6, and P2Y12 showed that compound 45 exhibited the highest degree of selectivity ( > 150-fold).
