4946-83-2

Usage

Chemical class

Anthraquinone derivatives

Type of compound

Synthetic organic compound

Molecular weight

289.33 g/mol

Common use

Dye intermediate, particularly in the textile industry

Known for

Vivid and durable color properties

Potential applications

Development of new materials and bioactive compounds

Structural features

Interesting and versatile

Health and environmental concerns

May pose hazards, requires proper regulation and management in handling and use

InChI:InChI=1/C19H17NO2/c21-18-13-7-2-3-8-14(13)19(22)17-15(18)9-6-10-16(17)20-11-4-1-5-12-20/h2-3,6-10H,1,4-5,11-12H2

Upstream product

• 110-89-4 piperidine 
• 82-34-8 1-nitroanthraquinone 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 84-65-1 9,10-phenanthrenequinone 

Downstream Products

• 3787-98-2 9-acetoxy-8-phenylazo-1,3,4,14a-tetrahydro-2H-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 
• 3777-52-4 9-acetoxy-8-(4-nitro-phenylazo)-1,3,4,14a-tetrahydro-2H-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 
• 3716-28-7 9-acetoxy-8-(2,5-dichloro-phenylazo)-1,3,4,14a-tetrahydro-2H-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 
• 3777-53-5 9-benzoyloxy-8-(4-nitro-phenylazo)-1,3,4,14a-tetrahydro-2H-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 
• 5828-38-6 9-acetoxy-8-p-tolylazo-1,3,4,14a-tetrahydro-2H-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 
• 5823-79-0 9-benzoyloxy-1,2,3,4-tetrahydro-anthra[1,9-de]pyrido[2,1-b][1,3]oxazine 

Relevant academic research and scientific papers

Synthesis and electrochemical, spectral, and biological evaluation of novel 9,10-anthraquinone derivatives containing piperidine unit as potent antiproliferative agents

The present study describes the synthesis and electrochemical, spectral and biological evaluation of new 9,10-anthraquinone derivatives containing one or two piperidine units incorporated in the different positions of the anthraquinone scaffold. The authors focused their efforts on the characterization of the obtained derivatives using the NMR and IR techniques and on the analysis of the molecules properties using the UV-VIS spectroscopy in the DMSO solution. Additionally, the electrochemical investigation of the compounds was performed using the cyclic voltammetry at the GC (glassy carbon) electrode in the DMSO solution. The primary aim of this study was to determine the antiproliferative activity of the obtained compounds. All novel anthraquinone derivatives containing piperidine unit in the structure were tested in vitro against four human cancer cell lines—HL-60, LoVo, HL-60/MX2, LoVo/Dx—which the latter two are drug-resistant. The tests also included the in vitro analyses of the antiproliferative activities against BALB/3T3 normal mouse fibroblasts cell lines. The results led to an interesting observation concerning the selectivity—all the derivatives exhibit potential anticancer activity against leukemic drug-resistant cell lines. Moreover, the most active compound 1-(piperidin-1-yl)-9,10-anthraquinone 1 inhibited also the proliferation of the colon cancer cell lines, distinctly overcoming the drug-resistance. Its activity towards the cancer cell lines was 5–8 times higher than the activity against normal fibroblasts cell line, which can suggest its selectivity towards cancer cells.

Amide Ion Formation and N-Alkylation of Aminoanthraquinones in the presence of Potassium Hydroxide in Dimethyl Sulfoxide

Amide ions were formed by the deprotonation of the amino group of amino group of amino- and (monoalkylamino)anthroquinones in the presence of powdered potassium hydroxide in dimethyl sulfoxide (DMSO).Under a nitrogen atmosphere these amide ions changed to their radical anions.The amide ions of 1-aminoanthroquinones reacted with excess alkyl halides to yield 1-alkylaminoanthraquinones, while the N-alkylation of 2-aminoanthraquinones afforded 2-alkylaminoanthraquinones in good yields. 2-Aminobenzophenone underwent mono-N-alkylation, while 4-aminoazobenzene and p-nitroaniline underwent di-N-alkylation.It was also found that carbanion of DMSO easily attacked the carbonyl group of the (dialkylamino)anthraquinones.

Novel, Direct Amination of Anthraquinone by Rhodium(I) Complexes

In the presence of certain rhodium(I) complexes, anthraquinone was found to react with amines to give the 1-alkylaminoanthraquinones, along with small amounts of the 1,4-bis(alkylamino)anthraquinones; this direct amination characteristically occurs only at the α-position of anthraquinone.