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HomeProduct name listBisantrene

Bisantrene

Bisantrene Structural

What is Bisantrene?

Originator

Bisantrene hydrochloride,ZYF Pharm Chemical

The Uses of Bisantrene

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

Properties of Bisantrene

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)
color  Orange to red

Safety information for Bisantrene

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H302:Acute toxicity,oral
H400:Hazardous to the aquatic environment, acute hazard
Precautionary Statement Codes P273:Avoid release to the environment.

Computed Descriptors for Bisantrene

InChIKey NJSMWLQOCQIOPE-OCHFTUDZSA-N
SMILES C1(/C=N/NC2=NCCN2)=C2C=CC=CC2=C(/C=N/NC2=NCCN2)C2C=CC=CC1=2

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