78186-34-2

Bisantrene Dihydrochloride: C22H22N8-2HCl. [71439-68-4]. Obtained from ethanol as an orange crystalline solid. The hemihydrate melts at 288-289°C (decomposition). UV absorption maximum (water): 260, 415 nm (ε72700, 16300).

Bisantrene hydrochloride,ZYF Pharm Chemical

Antineoplastic.

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.

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.).

Antineoplastic

Bisantrene dihydrochloride is an antineoplastic agentMDR1 substrateDNA intercalatorand topoisomerase II poison. Cancer cells th at develop resistance to bisantrene tend to overexpress P-glycoprotein. Bisantrene can be used to select for P-glycoprotein-mediated multiple drug resistance. The data suggest th at bisantrene is an excellent substrate for P-glycoprotein.''Bisantrene is an anthracene bishydrazone derivativewhich has antitumor activity.

Store at -20°C