Bisantrene Chemical Properties

Boiling point:

646.3±65.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

deionized water: soluble8mg/mL

form 

solid

pka

9.78±0.10(Predicted)

InChIKey

NJSMWLQOCQIOPE-OCHFTUDZSA-N

SMILES

C1(/C=N/NC2=NCCN2)=C2C=CC=CC2=C(/C=N/NC2=NCCN2)C2C=CC=CC1=2

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50/53

Safety Statements 

60-61

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

Bisantrene Usage And Synthesis

Originator

Bisantrene hydrochloride,ZYF Pharm Chemical

Uses

Antineoplastic.

Definition

ChEBI: A hydrazone resulting from the formal condensation of both of the aldehyde groups of anthracene-9,10-dicarbaldehyde with 2-hydrazinyl-4,5-dihydro-1H-imidazole.

Manufacturing Process

A 33.0 g (0.135 mole) of 2-methylthio-2-imidazoline hydroiodide is dissolved in 300 ml of water and treated with 8 ml (0.16 mole) of hydrazine hydrate. The mixture is stirred at room temperature for 20 hours and then taken to dryness under reduced pressure. The residue is dissolved in 250 ml of water and again taken to dryness under reduced pressure. The residue is redissolved in 250 ml of water and added to a mixture of 250 ml of water, 25 ml of concentrated hydrochloric acid and 25 g of silver oxide. The resulting mixture is stirred on a steam bath for 4 hours and then filtered. The filtrate is reduced to dryness under reduced pressure. The residue is dissolved in 300 ml of ethanol and 20 ml of water at the boil, clarified and cooled at -10°C. The precipitate is collected, washed with ethanol and ether and dried at 60°C and then 110°C under reduced pressure. Yield of the 2-hydrazino-2- imidazoline hydrochloride 11.6 g, melting point 177-180°C.
The 2-hydrazino-2-imidazoline monohydrochloride is converted to the dihydrochloride by treatment with ethanol and concentrated hydrochloric acid. A suspension of 3.46 g of the 2-hydrazino-2-imidazoline dihydrochloride and 2.34 g of 9,10-anthracenedicarboxaldehyde in 100 ml of ethanol is stirred and heated under reflux for two hours. The mixture is cooled and the solid is collected and washed with ethanol giving the desired product as a crystalline orange solid, m.p. 288-289°C (dec.).

Therapeutic Function

Antineoplastic

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