144675-97-8

Basic information

• Product Name: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2)
• Synonyms: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2);Bbr 2778;Pixantrone maleate;6,9-Bis[(2-aminoethyl)amino]benz[g]isoquinoline-5,10-dione (2Z)-2-butenedioate (1:2);6,9-Bis((2-aminoethyl)amino)benzo[g]isoquinoline-5,10-dione maleate;Dimalate salt
• CAS NO: 144675-97-8
• Molecular Formula: C21H23N5O6
• Molecular Weight: 441.43722
• EINECS: 1308068-626-2
• Product Categories: Inhibitors
• Mol File: 144675-97-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 192°
• Boiling Point: 650 °C at 760 mmHg
• Flash Point: 346.9 °C
• Appearance: /
• Vapor Pressure: 8.89E-17mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2)(CAS DataBase Reference)
• NIST Chemistry Reference: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2)(144675-97-8)
• EPA Substance Registry System: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2)(144675-97-8)

Safety Data

• Hazardous Substances Data: 144675-97-8(Hazardous Substances Data)

Usage

Chemical Properties

Blue Solid

Uses

Different sources of media describe the Uses of 144675-97-8 differently. You can refer to the following data:
1. Pixantrone is an antineoplastic drug belonging to group of antitumor antibiotics. Pixantrone is an anlogue of Mitoxantrone (M373425) and is just as potent in the treatment of multiple sclerosis with f ewer toxic effects on cardiac tissue. Studies suggest that Pixantrone significantly reduces amyloid beta (A beta(1-42)) neurotoxicity, a mechanism implicated in Alzheimer's disease.
2. Pixantrone is an antineoplastic drug belonging to group of antitumor antibiotics. Pixantrone is an anlogue of Mitoxantrone (M373425) and is just as potent in the treatment of multiple sclerosis with fewer toxic effects on cardiac tissue. Studies suggest that Pixantrone significantly reduces amyloid beta (A beta(1-42)) neurotoxicity, a mechanism implicated in Alzheimer''s disease.

InChI:InChI=1/C17H19N5O2.2C4H4O4/c18-4-7-21-12-1-2-13(22-8-5-19)15-14(12)16(23)10-3-6-20-9-11(10)17(15)24;2*5-3(6)1-2-4(7)8/h1-3,6,9,21-22H,4-5,7-8,18-19H2;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+

Upstream product

• 490-11-9 3,4-pyridinecarboxylic acid 
• 110-16-7 maleic acid 
• 144510-94-1 6,9-bis<<2-ethyl>amino>benzoisoquinoline-5,10-dione 
• 123-31-9 hydroquinone 
• 4664-08-8 cinchomeronic anhydride 

Relevant articles and documents

A cedar Joan maleic acid salt preparation method

The invention provides a pixantrone maleate synthesis method which has the advantages of high yield, low impurity content, simple process and easiness in large-scale production. In the method, pyridine-3,4-dicarboxylic acid is used as a starting raw material which reacts with acetic anhydride to obtain pyridine-3,4-dicarboxylic anhydride; the pyridine-3,4-dicarboxylic anhydride conducts an Friedel-Crafts acylation reaction with 1,4-difluorobenzene, and the obtained mixture is subjected to catalytic cyclization to obtain a key intermediate; the intermediate reacts with amino-protected ethylenediamine to obtain protecting group-containing pixantrone; and after that, deprotection and salifying are performed to obtain the target product. In the Friedel-Crafts acylation reaction of the method, an n-hexane solution of sulfuric acid is used as a catalyst, thus the use is convenient, the aftertreatment is simple, and the potential risk in production is eliminated; the Cbz or Fmoc protected ethylenediamine reacts with substituted anthraquinone and then the protecting group is removed through catalytic hydrogenation to obtain pixantrone; the process effectively inhibits side reactions and reduces the impurity content; and meanwhile, the aftertreatment is simplified, and the yield increase is facilitated.

Preparation method of pixantrone dimaleate

The invention relates to a preparation method of antitumor drug pixantrone dimaleate. The method includes the steps of: i) subjecting the compound 5(6, 9-bis[2-(N-Boc-amino)ethylamino]benzo[g]isoquinoline-5, 10-dione) to Boc protection removal reaction in dichloromethane (DCM) and trifluoroacetic acid (TFA), and letting the reaction generated reactant solution enter the next-step reaction directly without treatment; ii) employing a maleic acid ethanol solution to carry out acid exchange reaction on the reactant solution obtained in step i), and performing filtering to obtain a pixantrone dimaleate crude product. The method not only simplifies the operation process, greatly shortens the reaction time, improves production efficiency, but also can well control and remove impurities, especially a genotoxic impurities having potential serious hazard to the human body.