Benz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2)

Base Information

• Chemical Name: Benz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2)
• CAS No.: 144675-97-8
• Molecular Formula: C25H27N5O10
• Molecular Weight: 557.51
• European Community (EC) Number: 680-661-5
• NSC Number: 752341
• NCI Thesaurus Code: C82398
• Mol file: 144675-97-8.mol

Synonyms:5,8-bis((2-aminoethyl)amino)-2-aza-anthracene-9,10-dione;5,8-bis(2-aminoethylamino)-2-azaanthracene-9,10-dione;6,9-AEA-BIQDO;6,9-bis((2-aminoethyl)amino)benzo(g)isoquinoline-5,10-dione;BBR 2778;BBR-2778;BBR2778;pixantrone

Chemical Property of Benz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2)

Chemical Property:

• Vapor Pressure: 8.89E-17mmHg at 25°C
• Melting Point: 192°
• Boiling Point: 650 °C at 760 mmHg
• Flash Point: 346.9 °C
• PSA: 197.73000
• LogP: 1.85660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 441.16483347
• Heavy Atom Count: 32
• Complexity: 591

Purity/Quality:

98%,99%, ^*data from raw suppliers

PixantroneDimaleate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1NCCN)C(=O)C3=C(C2=O)C=NC=C3)NCCN.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC(=C2C(=C1NCCN)C(=O)C3=C(C2=O)C=NC=C3)NCCN.C(=C\C(=O)O)\C(=O)O
• Recent EU Clinical Trials: A multicentre, phase II, open label, single arm study of pixantrone in patients with CD20-positive relapsed or refractory aggressive non-Hodgkin lymphoma treated with rituximab, ifosfamide and etoposide.
• Uses: 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. 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.

Technology Process of Benz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2)

There total 7 articles about Benz[g]isoquinoline-5,10-dione, 6,9-bis[(2-aminoethyl)amino]-, (2Z)-2-butenedioate (1:2) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.3%

6,9-bis[2-(N-tert-butoxycarbonylamino)ethylamino]benzo[g]isoquinoline-5,10-dione + maleic acid (110-16-7,26099-09-2) → Pixantrone maleate (144675-97-8)

Guidance literature:

6,9-bis[2-(N-tert-butoxycarbonylamino)ethylamino]benzo[g]isoquinoline-5,10-dione; With trifluoroacetic acid; In dichloromethane; at 20 - 25 ℃; for 3h; Autoclave;

maleic acid; In ethanol; dichloromethane; at 20 - 25 ℃; for 17h; Temperature; Concentration; Autoclave;

Reference yield: 74.9%

6,9-bis[(benzyloxycarbonylaminoethyl)amino]benzo[g]isoquinoline-5,10-dione + maleic acid (110-16-7,26099-09-2) → Pixantrone maleate (144675-97-8)

Guidance literature:

6,9-bis[(benzyloxycarbonylaminoethyl)amino]benzo[g]isoquinoline-5,10-dione; With palladium on activated charcoal; hydrogen; acetic acid; In water; at 20 ℃; for 16h; under 2585.81 Torr; Autoclave;

maleic acid; In water; at 20 ℃; pH=3 - 5;

Reference yield:

cinchomeronic anhydride (4664-08-8) → Pixantrone maleate (144675-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 45percent silica gel supported phosphoric acid / cyclohexane / 5 h / Reflux

2: potassium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 60 °C

3: potassium hydroxide / 12 h / 20 °C / pH 3.4 / Inert atmosphere

With potassium carbonate; potassium hydroxide; In 1-methyl-pyrrolidin-2-one; cyclohexane;

upstream raw materials:

maleic acid

cinchomeronic anhydride

hydroquinone

6,9-bis<<2-ethyl>amino>benzoisoquinoline-5,10-dione

Refernces

• 1、 -. "6, 9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5, 10-dione dimaleate and synthesis technology thereof". . . Retrieved 2017/03/18.
• 2、 -. "6,9-bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione and its dimaleate salt". . . Retrieved 2008/06/13.