70477-04-2

Basic information

• Product Name: 1,4-bis{[2-(diethylamino)ethyl]amino}anthracene-9,10-dione
• Synonyms: 1,4-Bis((2-(diethylamino)ethyl)amino)-9,10-anthracenedione; 9,10-Anthracenedione, 1,4-bis((2-(diethylamino)ethyl)amino)-
• CAS NO: 70477-04-2
• Molecular Formula: C₂₆H₃₆N₄O₂
• Molecular Weight: 436.5896
• Mol File: 70477-04-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 618.2°C at 760 mmHg
• Flash Point: 327.7°C
• Density: 1.156g/cm³
• Vapor Pressure: 3.29E-15mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 1,4-bis{[2-(diethylamino)ethyl]amino}anthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis{[2-(diethylamino)ethyl]amino}anthracene-9,10-dione(70477-04-2)
• EPA Substance Registry System: 1,4-bis{[2-(diethylamino)ethyl]amino}anthracene-9,10-dione(70477-04-2)

Safety Data

• Hazardous Substances Data: 70477-04-2(Hazardous Substances Data)

Upstream product

• 109-89-7 diethylamine 
• 111228-28-5 1,4-bis<<2-<(p-toluenesulfonyl)oxy>ethyl>amino>anthracene-9,10-dione 
• 60-29-7 diethyl ether 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 100-36-7 N,N-diethylethylenediamine 
• 4471-41-4 1,4-bis-(2-hydroxyethylamino)anthraquinone 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 

Relevant articles and documents

Anti-cancer compounds

Compounds of formula (I) STR1 in which R1, R2, R3 and R4 are each separately selected from hydrogen, X, NH--A--NHR and NH--A--N(O)R'R" wherein X is hydroxy, halogeno, amino, C1-4 alkoxy or C2-8 alkanoyloxy, A is a C2-4 alkylene group with a chain length between NH and NHR or N(O)R'R" of at least 2 carbon atoms and R, R' and R" are each separately selected from C1-4 alkyl groups and C2-4 hydroxyalkyl and C2-4 dihydroxyalkyl groups in which the carbon atom attached to the nitrogen atom does not carry a hydroxy group and no carbon atom is substituted by two hydroxy groups, or R' and R" together are a C2-6 alkylene group which with the nitrogen atom to which R" and R" are attached forms a heterocyclic group having 3 to 7 atoms in the ring, but with the proviso that at least one of R1 to R4 is a group NH--A--N(O)R'R", and physiologically acceptable salts thereof are of value in the treatment of cancer.

Comparative Computer Graphics and Solution Studies of the DNA Interaction of Substituted Anthraquinones Based on Doxorubicin and Mitoxantrone

1-amino>- and 1,4-, 1,5-, and 1,8-bisamino>anthraquinones are shown to intercalate into DNA.Computer graphics modelling of their intercalation into the self-complementary deoxydinucleoside d(CpG) showed differences in binding properties.While the 1-substituted compound can bind from euther groove, the 1,8-disubstituted compound binds with both substituents in the major groove.In the-low energy state of the complex with the 1,5-disubstituted compound, this ligand "straddles" the site with a substituent in each groove-to do this, the compound must bind to a non-base-paired region, so inducing base pairing.The 1,4-compound binds from the major groove; "straddling" is also possible if full minimization of deoxydinucleoside geometry is performed.The differences in binding mode and interaction energies are reflected in the affinities of interaction (1,5- > 1,4- >> 1,8- > 1-); also the antiproliferative effects in vitro are in general agreement with this ranking.