16517-70-7

Basic information

• Product Name: 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione
• Synonyms: 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione
• CAS NO: 16517-70-7
• Molecular Formula: C₁₄H₁₀N₂O₄
• Molecular Weight: 270.2402
• Mol File: 16517-70-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 635.3°Cat760mmHg
• Flash Point: 338°C
• Appearance: /
• Density: 1.683g/cm³
• Vapor Pressure: 9.78E-17mmHg at 25°C
• Refractive Index: 1.836
• CAS DataBase Reference: 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione(16517-70-7)
• EPA Substance Registry System: 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione(16517-70-7)

Safety Data

• Hazardous Substances Data: 16517-70-7(Hazardous Substances Data)

Usage

Uses

5,8-Diamino-1,4-dihydroxyanthraquinone is an inhibitor of protein kinase CK2.

InChI:InChI=1/C14H10N2O4/c15-5-1-2-6(16)10-9(5)13(19)11-7(17)3-4-8(18)12(11)14(10)20/h1-4,17-18H,15-16H2

Upstream product

• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 131401-54-2 1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione 
• 860731-28-8 1,4-dimethoxy-5,8-bis-(toluene-4-sulfonylamino)-anthraquinone 
• 160283-85-2 1,4-diphthaliloamino-5,8-bis(phenylmethoxy)-9,10-anthracenedione 
• 91440-79-8 1,4-di(benzyloxy)-5,8-dichloro-9,10-dihydro-9,10-anthracenedione 
• 160283-84-1 1,4-diamino-5,8-bis(phenylmethoxy)-9,10-anthracenedione 
• 137369-80-3 1,4-diamino-5,8-dimethoxy-anthraquinone 
• 50380-56-8 1,4-dichloro-5,8-dimethoxy-9,10-anthracenedione 

Downstream Products

• 81-60-7 1,4,5,8-tetrahydroxy-anthraquinone 

Relevant articles and documents

Interaction of anthraquinone anti-cancer drugs with DNA:Experimental and computational quantum chemical study

Anthraquinones form the basis of several anticancer drugs. Anthraquinones anticancer drugs carry out their cytotoxic activities through their interaction with DNA, and inhibition of topoisomerase II activity. Anthraquinones (AQ4 and AQ4H) were synthesized and studied along with 1,4-DAAQ by computational and experimental tools. The purpose of this study is to shade more light on mechanism of interaction between anthraquinone DNA affinic agents and different types of DNA. This study will lead to gain of information useful for drug design and development. Molecular structures were optimized using DFT B3LYP/6-31?+?G(d). Depending on intramolecular hydrogen bonding interactions two conformers of AQ4 were detected and computed as 25.667?kcal/mol apart. Molecular reactivity of the anthraquinone compounds was explored using global and condensed descriptors (electrophilicity and Fukui functions). Molecular docking studies for the inhibition of CDK2 and DNA binding were carried out to explore the anti cancer potency of these drugs. NMR and UV-VIS electronic absorption spectra of anthraquinones/DNA were investigated at the physiological pH. The interaction of the three anthraquinones (AQ4, AQ4H and 1,4-DAAQ) were studied with three DNA (calf thymus DNA, (Poly[dA].Poly[dT]) and (Poly[dG].Poly[dC]). NMR study shows a qualitative pattern of drug/DNA interaction in terms of band shift and broadening. UV-VIS electronic absorption spectra were employed to measure the affinity constants of drug/DNA binding using Scatchard analysis.

Synthesis of 1,4-Diamino-5,8-dihydroxy-9,10-anthracenedione via Gabriel Reaction

-