78186-34-2

Basic information

• Product Name: Bisantrene
• Synonyms: BISANTRENE;BISANTRENE HCL;9，10-An-thracenedicarboxaldehyde bis[(4，5-dihydro-1H-imidazol-2-y1)hydrazone];ADAH;CL-216942;NSC-337766;Orange Crush;Zantrene
• CAS NO: 78186-34-2
• Molecular Formula: C₂₂H₂₂N₈
• Molecular Weight: 398.46
• Mol File: 78186-34-2.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 646.3 °C at 760 mmHg
• Flash Point: 344.7 °C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 1.36E-16mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: room temp
• Solubility: deionized water: soluble8mg/mL
• CAS DataBase Reference: Bisantrene(CAS DataBase Reference)
• NIST Chemistry Reference: Bisantrene(78186-34-2)
• EPA Substance Registry System: Bisantrene(78186-34-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 78186-34-2(Hazardous Substances Data)

Usage

Description

Bisantrene, also known as ChEBI, is a hydrazone derived from the formal condensation of both aldehyde groups of anthracene-9,10-dicarbaldehyde with 2-hydrazinyl-4,5-dihydro-1H-imidazole. It is a compound with significant potential in the field of medicine, particularly in cancer treatment.

Uses

Used in Antineoplastic Applications:
Bisantrene is used as an antineoplastic agent, which means it is employed in the treatment of various types of cancer. It works by targeting and inhibiting the growth of cancer cells, making it a valuable tool in the fight against neoplastic diseases.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Bisantrene is used as an active pharmaceutical ingredient (API) for the development of cancer treatment drugs. Its unique chemical structure allows it to be formulated into various drug forms, such as tablets, capsules, or injectables, to maximize its therapeutic potential.
Used in Research and Development:
Bisantrene is also used in research and development for the discovery of new cancer treatment strategies. Its chemical properties make it an interesting candidate for further study, as it may lead to the development of novel drugs with improved efficacy and reduced side effects.

Originator

Bisantrene hydrochloride,ZYF Pharm Chemical

Therapeutic Function

Antineoplastic

InChI:InChI=1/C22H22N8/c1-2-6-16-15(5-1)19(13-27-29-21-23-9-10-24-21)17-7-3-4-8-18(17)20(16)14-28-30-22-25-11-12-26-22/h1-8,13-14H,9-12H2,(H2,23,24,29)(H2,25,26,30)/b27-13-,28-14-

Synthetic route

sodium tetrachloroaurate(III) dihydrate + bisantrene (78186-34-2) → C22H22N8*2H(1+)*2AuCl4(1-)

Conditions	Yield
In methanol; dichloromethane at 50℃; for 12h; Solvent; Temperature;	70%

4H2O*HAuCl4 + bisantrene (78186-34-2) → C22H22N8*2H(1+)*2AuCl4(1-)

Conditions	Yield
In methanol at 4℃; for 12h;	70%

chlorophosphoric acid diphenyl ester (2524-64-3) + bisantrene (78186-34-2) → <9,10-anthracenediylbis>bis tetraphenyl ester

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane for 3h;	52%

KAuCl4 + 4H2O*HAuCl4 + bisantrene (78186-34-2) → C22H22N8*2H(1+)*2AuCl4(1-)

Conditions	Yield
In methanol; propan-1-ol; dichloromethane at 40℃; for 12h;	50%

diethyl chlorophosphate (814-49-3) + bisantrene (78186-34-2) → <9,10-anthracenediylbis>bis tetraethyl ester (115314-35-7)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane for 3h;	32%

diethyl chlorophosphate (814-49-3) + bisantrene (78186-34-2) → <9,10-anthracenediylbis>bis tetraethyl ester (115314-35-7) + <2-<<<10-<<(4,5-dihydro-1H-imidazol-2-yl)hydrazono>methyl>-9-anthracenyl>methylene>hydrazino>-4,5-dihydro-1H-imidazol-1-yl>phosphonic acid diethyl ester (115314-43-7)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; water In dichloromethane for 3h;	A 12.50 g B 4.50 g

diethyl cyanophosphonate (2942-58-7) + bisantrene (78186-34-2) → <9,10-anthracenediylbis>bis tetraethyl ester (115314-35-7)

Conditions	Yield
In N,N-dimethyl-formamide for 5h;	655 mg

bisantrene (78186-34-2) + methyl iodide (74-88-4) → C26H30N8*2HI (81067-93-8)

Conditions	Yield
In N,N-dimethyl-formamide for 2.75h; Ambient temperature; Yield given;

bisantrene (78186-34-2) → <9,10-anthracenediylbis>bis (115314-36-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 32 percent / N,O-bis(trimethylsilyl)acetamide / CH2Cl2 / 3 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h View Scheme
Multi-step reaction with 2 steps 1: 12.50 g / N,O-bis(trimethylsilyl)acetamide, water / CH2Cl2 / 3 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h View Scheme
Multi-step reaction with 2 steps 1: 655 mg / dimethylformamide / 5 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h View Scheme

bisantrene (78186-34-2) → <2-<<<10-<<(4,5-dihydro-1H-imidazol-2-yl)hydrazono>methyl>-9-anthracenyl>methylene>hydrazino>-4,5-dihydro-1H-imidazol-1-yl>phosphonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.50 g / N,O-bis(trimethylsilyl)acetamide, water / CH2Cl2 / 3 h 2: 1.) triphenylphosphine, iodotrimethylsilane, 2.) water / 1.) methylene chloride, 30 min, 2.) acetone View Scheme

bisantrene (78186-34-2) → <2-<<<10-<<(4,5-dihydro-1H-imidazol-2-yl)ethylhydrazono>methyl>-9-anthracenyl>methylene>hydrazino>-4,5-dihydro-1H-imidazol-1-yl>phosphonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.50 g / N,O-bis(trimethylsilyl)acetamide, water / CH2Cl2 / 3 h 2: 1.) iodotrimethylsilane, 2.) water / 1.) methylene chloride, 30 min, 2.) acetone View Scheme

bisantrene (78186-34-2) → disodium <9,10-anthracenediylbis>bis

Conditions	Yield
Multi-step reaction with 3 steps 1: 32 percent / N,O-bis(trimethylsilyl)acetamide / CH2Cl2 / 3 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h 3: 629 mg / aq. NaOH View Scheme
Multi-step reaction with 3 steps 1: 12.50 g / N,O-bis(trimethylsilyl)acetamide, water / CH2Cl2 / 3 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h 3: 629 mg / aq. NaOH View Scheme
Multi-step reaction with 3 steps 1: 655 mg / dimethylformamide / 5 h 2: 1.) iodotrimethylsilane, 2.) H2O / 1.) methylene chloride, o deg C, 30 min, 2.) acetone, 16 h 3: 629 mg / aq. NaOH View Scheme