24429-49-0

Usage

Class

Anthracene derivatives

Common uses

Fluorescent dye for biological staining, pH indicator, synthesis of organic compounds, reagent in analytical chemistry

Solubility

Water-soluble

Specific form

Monosodium salt, highly soluble in aqueous solutions

Potential applications

Photovoltaics, materials science, due to photochemical and photophysical properties

Upstream product

• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 82-45-1 1-amino-9,10-anthracenedione 
• 66583-20-8 1-amino-2-mercapto-9,10-antraquinone sodium salt 

Downstream Products

• 82-45-1 1-amino-9,10-anthracenedione 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 81-49-2 1-amino-2, 4-dibromoanthraquinone 

Relevant academic research and scientific papers

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs

Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminic acid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.

Structure-activity relationships of novel P2-receptor antagonists structurally related to Reactive Blue 2

P2 membrane receptors for nucleotides represent significant targets for experimental pharmacology and drug research. In earlier publications, we have shown that Reactive Blue 2 (RB 2), one of the most widely used P2-receptor antagonists, displays only moderate affinity and does not discriminate between native P2X- and P2Y-receptor subtypes. In the present study we have pharmacologically evaluated a series of 15 synthesized and re-evaluated four commercially obtained and chromatographically purified RB 2 type anthraquinone derivatives on contractions of the rat vas deferens (RVD) elicited by α,β-methylene ATP (α,β-meATP), mediated by P2X 1-receptors, and relaxations of the carbachol-precontracted guinea-pig taenia coli (GPTC) elicited by adenosine 5′-O-(2- thiodiphosphate) (ADPβS), mediated by P2Y1-like receptors. Based on the structure-activity relationships (SAR) it is concluded that hydrophobic interactions of aromatic π-electron systems, hydrogen bonds with nitrogen as donor and acceptor atoms, and, particularly, position, conformational distance and number of anionic sulfonate groups are of great importance for the blockade of the two native P2-receptor subtypes. We have also identified novel, for the most part reversible antagonists that bind with higher affinity and improved subtype selectivity in comparison to RB 2. In particular, 1-amino-4-{4-[4- chloro-6-(2-sulfonatophenylamino)-[1,3,5]triazine-2-ylamino]-2- sulfonatophenylamino}-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid trisodium salt (MG 50-3-1) is the most potent antagonist at the P2Y 1-like-receptors of the GPTC reported so far (IC50 = 4.6:nM). It is significantly less potent as reversible antagonist at the P2X1-receptors of the RVD (IC50 = 2.8 μM). Thus, MG 50-3-1 represents a selective pharmacological tool and may be a lead compound for future investigations.

ELECTROCHEMICAL REDUCTION OF SODIUM 1-AMINO-4-BROMO-ANTHRAQUINONE-2-SULFONATE

The product from electrochemical reduction of sodium 1-amino-4-bromoanthraquinone-2-sulfonate in an alkaline medium is sodium 1-aminoanthraquinone-2-sulfonate.In the presence of copper sulfate disodium 4,4'-diamino-1,1'-bianthraquinonyl-3,3'-disulfonate is also formed.In the presence of copper sulfate and oxygen sodium 1-amino-4-hydroxyanthraquinone-2-sulfonate is also formed.It is suggested that during the electrochemical reduction, as in the reduction of 1-amino-4-bromoanthraquinone-2-sulfonic acid with aromatic amines, these products are formed by a mechanism involving an electron transfer stage.

Photochemical Substitution of Amino- and Hydroxy-anthraquinones

Irradiation of 1-aminoanthraquinone with visible light in the presence of an excess of either sodium sulphite or sulphide in 50percent aqueous pyridine gives exclusively sodium 1-aminoanthraquinone-2-sulphonate and -2-thiolate, respectively, in good yield.Under similar conditions with sodium sulphite, 1-methylamino-, 1-amino-4-chloro-, and 1-amino-5-chloro-anthraquinone give the respective sodium 2-sulphonate only, while 2-aminoanthraquinone gives the sodium 3-sulphonate.In contrast, 1-hydroxyanthraquinone gives a mixture of the sodium 2- and 4-sulphonates and disodium 2,4-disulphonates.The different substitution pattern observed for 1-amino- and 1-hydroxy-anthraquinone has been rationalised by application of semi-empirical molecular orbital theory.