128-95-0Relevant articles and documents
Carbon-13 NMR Spectra of Anthraquinone-Derived Dyes
Rubin, I. B.,Buchanan, M. V.
, p. 161 - 165 (1985)
The 13C NMR spectra of six anthraquinone-derived dyes, namely benzanthrone, 1-(methylamino)anthraquinone, 1,4-di-p-toluidinoanthraquinone, 1,4-diamino-2,3-dihydroanthraquinone, 1,4-diaminonanthraquinone and dibenzochrysenedione, have been measured.The chemical shift assignments were achieved by elucidation of the coupling patterns of the fully coupled spectra and by comparison with the chemical shifts of other anthraquinone derivatives and other model compounds.One- and three-bond carbon-hydrogen coupling constants are also reported.
A new Synthesis of 1-Amino-4-butylaminoanthraquinone from 1-Aminoanthraquinone Promoted by Metal Ions
Yoshida, Katsuhira,Matsuoka, Masaru,Yamashita, Yoshio,Kitao, Teijiro
, p. 2552 - 2554 (1980)
In the presence of some metal ions and atmospheric oxygen, 1-aminoanthraquinone (1) reacts readily with butylamine to give 1-amino-4-butylaminoanthraquinone(2a), along with a small amount of 1,4-diaminoanthraquinone, which is produced by the dealkylation of 2a.The activity of the metal ions decreased in the following order: Co(II) >> Ni(II) above Cu(II) above Al(III).The reaction is remarkably affected by the substitution of an alkyl group into the amino group of 1, the addition of a chelating agent, the counter anion of metal ions, and the reaction temperature.By the use of cobalt(II) chloride, the reaction proceeds most smoothly at about 30 deg C.Both anthraquinone and 2-aminoanthraquinone show no sign of the reaction under the same conditions.A possible mechanism involving the formation of a metal complex, followed by the nucleophilic attack of amine at the 4-position and the oxidative abstraction of the hydride anion by atmospheric oxygen is proposed.
Structure-activity relationships of novel P2-receptor antagonists structurally related to Reactive Blue 2
Gl?nzel, Markus,Bültmann, Ralph,Starke, Klaus,Frahm, August W.
, p. 1262 - 1276 (2007/10/03)
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.
Experimental and theoretical study of tautomerism in 1,4-bisanthracene-9,10-diones and their reduced forms
Morley, John. O.,Krapcho, A. Paul,Cummings, Douglas S.
, p. 287 - 292 (2007/10/03)
Treatment of leucoquinizarin 4a with methoxylamine hydrochloride (O-methylhydroxylamine hydrochloride) in oyridine led to tautomer 4e.Oxidation of 4e in refluxing nitrobenzene led to 1,4-diaminoanthracene-9,10-dione 1e while oxidation with manganese dioxide yielded 1,4-bis(methoxyimino)-2,3-dihydroanthracene-9,10-dione 6.Attempted diplacement of the fluorides from 1,4-difluroanthracene-9,10-dione by methoxylamine in dimethyl sulfoxide led to 9,10-dihydroxy-1,4-bis(methoxyimino)anthracene 2h instead of the anticipated bis(methoxyamino) tautomer 1h.Calculations have been carried out on some of these derivatives using the 3-21G basis set and the results for 2h compared with X-ray data from a single crystal.The calculated results show that that 1h is marginally preferred over 2h by 0.68 kcal mol-1.The reduced forms show the opposite trend with 4e preferred by 11.3 kcal mol-1 over 3e in line with NMR data recorded in chloroform.The presence of an oxygen atom adjacent to the nitrogen atom in the methoxyimine substituent forces a tetrahedral conformation at nitrogen resulting in a destabilization of the anthracene-9,10-dione tautomers 1h and 3e.
Reactions of 2,3-Dihydro-9,10-anthracenedione (Leucoquinizarin) with Hydrazine and Substituted Hydrazines
Krapcho, A. Paul,Avery, Kenneth L.,Shaw, Kenneth J.,Andrews, John D.
, p. 4960 - 4961 (2007/10/02)
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