Ametantrone

Base Information

• Chemical Name: Ametantrone
• CAS No.: 64862-96-0
• Molecular Formula: C22H28 N4 O4
• Molecular Weight: 412.54
• Hs Code.: 2922509090
• NSC Number: 196473
• UNII: PNT6041ST1
• DSSTox Substance ID: DTXSID60215153
• Nikkaji Number: J710.750A,J67.628D
• Wikidata: Q27286653
• NCI Thesaurus Code: C1342
• Pharos Ligand ID: Y6455TULCGSR
• Metabolomics Workbench ID: 144636
• ChEMBL ID: CHEMBL49442
• Mol file: 64862-96-0.mol

Synonyms:1,4-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-9,10-anthracenedione diacetate;ametantrone;ametantrone diacetate;ametantrone ion (1-);HAQ;NSC 196473;NSC 287513;NSC-196473;NSC-287513

Chemical Property of Ametantrone

Chemical Property:

• Vapor Pressure: 4.4E-21mmHg at 25°C
• Melting Point: 156-158 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 708.8°C at 760 mmHg
• PKA: 14.47±0.10(Predicted)
• Flash Point: 382.4°C
• PSA: 122.72000
• Density: 1.2344 (rough estimate)
• LogP: 1.37740
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 412.21105539
• Heavy Atom Count: 30
• Complexity: 513

Purity/Quality:

98% min ^*data from raw suppliers

Ametantrone >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C=CC(=C3C2=O)NCCNCCO)NCCNCCO
• Description: Ametantrone is an inhibitor of topoisomerase II. It induces double-strand breaks in SV40 DNA in the presence, but not absence, of topoisomerase II and induces single-strand breaks in DNA in NCI H187 cells. It also induces interstrand DNA cross-links in HeLa S3 cells at a minimum concentration of 4.1 μM. Ametantrone is cytotoxic to NCI H187 and HL-60 cells (IC50s = 112 and 0.44 μM, respectively). It inhibits tumor growth in a Ridgway osteogenic sarcoma mouse model when administered at a dose of 5 mg/kg, however, it increases tumor growth in mouse models of mammary adenocarcinoma and colon adenocarcinoma 11a.

Technology Process of Ametantrone

There total 5 articles about Ametantrone 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: 94.0%

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2,79248-79-6) + 2-(2-Aminoethylamino)ethanol (111-41-1) → ametantrone (64862-96-0)

Guidance literature:

9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione; 2-(2-Aminoethylamino)ethanol; In acetonitrile; at 50 ℃; for 1h; Inert atmosphere;

With air; at 50 ℃; for 1h;

Reference yield: 85.0%

ethanolamine (141-43-5) + 1,4-bis<<2-<(p-toluenesulfonyl)oxy>ethyl>amino>anthracene-9,10-dione (111228-28-5) → ametantrone (64862-96-0)

Guidance literature:

In benzene; for 2h; Heating;

Reference yield: 36.0%

1,4-difluoroanthracene-9,10-dione (28736-42-7) + 2-(2-Aminoethylamino)ethanol (111-41-1) → ametantrone (64862-96-0)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 96h;

DOI:10.1002/cmdc.201000106

upstream raw materials:

ethanolamine

1,4-bis<<2-<(p-toluenesulfonyl)oxy>ethyl>amino>anthracene-9,10-dione

1,4-difluoroanthracene-9,10-dione

2-(2-Aminoethylamino)ethanol

Refernces

• 1、 Artigas, Gerard,Marchán, Vicente. "Synthesis and tau RNA binding evaluation of ametantrone-containing ligands". . p. 2155 - 2164. Retrieved 2015.
• 2、 Gianoncelli, Alessandra,Basili, Serena,Scalabrin, Matteo,Sosic, Alice,Moro, Stefano,Zagotto, Giuseppe,Palumbo, Manlio,Gresh, Nohad,Gatto, Barbara. "Rational design, synthesis, and DNA binding properties of novel sequence-selective peptidyl congeners of ametantrone". experimental part. p. 1080 - 1091. Retrieved 2011/02/21.