3274-19-9

Usage

Uses

Used in Pharmaceutical Industry:
N-anthraquinon-1-ylacetamide is used as a pharmaceutical agent for its potential to exhibit a range of biological activities. N-anthraquinon-1-ylacetamide is being studied for its ability to combat bacterial and fungal infections due to its antibacterial and antifungal properties. Additionally, its anti-inflammatory and antitumor characteristics suggest it may be utilized in the development of treatments for inflammatory conditions and cancer.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, N-anthraquinon-1-ylacetamide serves as a subject of research for its potential to contribute to the discovery of new drugs. Its structure and functional groups are of interest to scientists who aim to modify and optimize its properties for specific medical applications, including the enhancement of its therapeutic effects and the reduction of potential side effects.

Upstream product

• 63512-12-9 N-(anthracen-1-yl)acetamide 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 82-45-1 1-amino-9,10-anthracenedione 
• 60-35-5 acetamide 
• 75-36-5 acetyl chloride 
• 10165-25-0 1-acetylamino-4-chloro-anthraquinone 
• 60840-08-6 2-acetylamino-2'-carboxy-diphenylmethane 
• 610-49-1 1-aminoanthracene 
• 64-19-7 acetic acid 

Downstream Products

• 6937-74-2 1-amino-4-nitroanthraquinone 
• 2872-47-1 1-amino-4-chloroanthraquinone 
• 22281-18-1 naphtho[1',2',3':4,5]quino[2,1-b]quinazoline-5,10-dione 
• 82-45-1 1-amino-9,10-anthracenedione 
• 82-38-2 1-(methylamino)anthraquinone 

Relevant academic research and scientific papers

Microbial metabolism of 1-aminoanthracene by Beauveria bassiana

The carcinogen and mutagen, 1-aminoanthracene, was efficiently metabolized by the fungal strain Beauveria bassiana ATCC 7159 to yield three new metabolites identified as 1-acetamido-5-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthracene, 1-acetamido-8-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, and 1-acetamido-6-[(4′-O-methyl-β-d-glucopyranosyl)oxy]anthraquinone, together with 1-acetamidoanthracene and 1-acetamidoanthraquinone. Formation of these metabolites suggests that the metabolic pathways of 1-aminoanthracene in B. bassiana ATCC 7159 involve acetylation, oxidation, hydroxylation, and O-methylglucosylation.

Pd-catalyzed α-selective C(sp3)-H acetoxylation of amides through an unusual cyclopalladation mechanism

We report the first example of Pd-catalyzed site-selective α-C(sp3)-H oxidation/acetoxylation of amides through an unusual [4,6]-bicyclic metallacycle intermediate with 1-aminoanthraquinone as a new bidentate directing group. In addition to the distinct mechanism and high efficiency, the reaction is highly appealing due to the ample commercial source, low-cost, as well as easy removal and recycling of the auxiliary group.

Silica-supported boric acid catalyzed synthesis of dihydropyrimidin-2-ones, bis(indolyl)methanes, esters and amides

Silica-supported boric acid (H3BO3-SiO2) has been established as a green, efficient and recyclable catalyst for the synthesis of dihydropyrimidin-2-ones, bis(indolyl)methanes, and acetylation of alcohols, phenols, amines and thiols under solvent free conditions. The main features of the present method include clean reaction, mild conditions, low loading of environment friendly catalyst and easy workup procedure. The catalyst can be recycled at least five times without any significant loss in activity.

A New Acylation Catalyst

Cobalt(II) chloride catalyses the acylation of alcohols and amines with anhydrides in excellent yields.

SOME RELATIONSHIPS IN THE SYNTHESIS OF BIARYLS FROM HALOGENOANTHRAQUINONES

The effects of the solvent and the concentration of the reagents on the reaction path and on the results of the synthesis of biaryls from halogenoanthraquinones were investigated for the case of the reaction of 1-chloro-4-benzoylaminoanthraquinone with copper.The use of concentrated reaction mixtures and of donating aprotic dipolar solvents with copper-aryl halide ratios slightly exceeding an equimolar ratio leads to a reduction in the induction period and to an increase in the yield of the biaryls.This explained by interaction between the copmonents of the metal-aryl halide-solvent complex.

Photochemical Alkylamination of 1-Acylaminoanthraquinones

The photochemical reaction of 1-acylaminoanthraquinones (1) with primary aliphatic amines in benzene, in air, gave 1-acylamino-4-alkylaminoanthraquinones (2) in 56-78percent yields.The reaction was retarded by the addition of triplet quenchers.The quantum yield of the reaction increased on raising the amine concentration.A mechanism via addition of alkylamine to the triplet excited state of (1), followed by oxidation to give the products (2), is proposed.The regioselective 4-amination of (1) has been rationalized by means of the frontier orbital method.

EFFECT OF SRUCTURAL FACTORS ON THE FORMATION AND PROPERTIES OF ACYLAMINOANTHRAQUINONES

The N-methyl group prevents the acylation of α-aminoanthraquinones by acetic anhydride in the absence of acid catalysis.This is explained by hindrances for the abstraction of hydrogen atom from the 1-methylamino group, which is connected by an intramolecular hydrogen bond.Acid catalysis levels out the differences in the reactivity of the α-amino and α-methyl amino groups.The α-acetylamino groups have lower hydrolytic stability than the α-N-acetylmethylamino groups.These characteristics make it possible to realize a directed synthesis of acyl derivatives at theprimary or secondary α-amino groups of polyaminoanthraquinones.The introduction of acyl residues into the secondary α-amino groups completely excludes them conjugation with the anthraquinone ring, and an unexpectedly small hypsochromic shift of the absorption is observed in the 4-amino, 4-alkylamino, and particularly the 4-arylamino derivatives of 1-acylaminoanthraquinones.

Preparation and oxidation of 4-acylamino-anthrones

A 2-acylamino-2'-carboxy-diphenylmethane is treated with an acid condensing agent such as sulfuric acid or chlorosulfonic acid thereby to produce the corresponding 4-acylamino-anthrone which can then be oxidized, as with hydrogen peroxide or oxygen, to the corresponding 1-acylamino-anthraquinone.