Teloxantrone

Base Information

• Chemical Name: Teloxantrone
• CAS No.: 91441-48-4
• Molecular Formula: C₂₁H₂₅N₅O₄
• Molecular Weight: 411.461
• UNII: 96521WL61B
• DSSTox Substance ID: DTXSID70869080,DTXSID001317868
• Nikkaji Number: J246.128E
• Wikidata: Q27271867
• NCI Thesaurus Code: C1520
• ChEMBL ID: CHEMBL24329
• Mol file: 91441-48-4.mol

Synonyms:CI 937;CI-937;Dup 937;Dup-937;teloxantrone;teloxantrone hydrochloride

Chemical Property of Teloxantrone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 765.7°Cat760mmHg
• Flash Point: 416.9°C
• PSA: 131.67000
• Density: 1.41g/cm³
• LogP: 1.61990
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 411.19065430
• Heavy Atom Count: 30
• Complexity: 997

Purity/Quality:

96% ^*data from raw suppliers

TELOXANTRONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNCCN=C1C=CC2=C3C1=C(C4=C(C=CC(=O)C4=C3NN2CCNCCO)O)O
• Uses: Antineoplastic.

Technology Process of Teloxantrone

There total 6 articles about Teloxantrone 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:

2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<2-ethyl>amino>-7,10-bis(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one (104740-31-0) → 7,10-dihydroxy-2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<(2-methylamino)ethyl>amino>anthra<1,9-cd>pyrazol-6(2H)-one (91441-48-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 2.06667h; under 258.6 Torr; Parr shaker;

DOI:10.1002/jhet.5570260117

Reference yield:

5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]-pyrazol-6(2H)-one (91441-59-7) → 7,10-dihydroxy-2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<(2-methylamino)ethyl>amino>anthra<1,9-cd>pyrazol-6(2H)-one (91441-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / 3 h / 132 °C

2: H₂ / 20percent Pd(OH)2/C / acetic acid / 4 h / 25 °C / 760 Torr

With hydrogen; palladium dihydroxide; In acetic acid;

DOI:10.1021/jm00384a021

Reference yield:

2-<2-<(2-hydroxyethyl)(phenylmethyl)amino>ethyl>-5-<<2-ethyl>amino>-7,10-bis(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one (105158-36-9) → 2-[2-(2-Hydroxy-ethylamino)-ethyl]-5-(2-methylamino-ethylamino)-1,2-dihydro-dibenzo[cd,g]indazole-6,7,10-triol (123844-10-0) + 7,10-dihydroxy-2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<(2-methylamino)ethyl>amino>anthra<1,9-cd>pyrazol-6(2H)-one (91441-48-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 2.06667h; under 258.6 Torr; Yield given; Parr shaker;

DOI:10.1002/jhet.5570260117

upstream raw materials:

2-<2-<(2-hydroxyethyl)amino>ethyl>-5-<<2-ethyl>amino>-7,10-bis(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one

2-<2-<(2-hydroxyethyl)(phenylmethyl)amino>ethyl>-5-<<2-ethyl>amino>-7,10-bis(phenylmethoxy)anthra<1,9-cd>pyrazol-6(2H)-one

(2-{7,10-Dihydroxy-2-[2-(2-hydroxy-ethylamino)-ethyl]-6-oxo-2,6-dihydro-dibenzo[cd,g]indazol-5-ylamino}-ethyl)-methyl-carbamic acid benzyl ester

5-chloro-2-[2-[(2-hydroxyethyl)amino]ethyl]-7,10-bis(phenylmethoxy)anthra[1,9-cd]-pyrazol-6(2H)-one

Refernces

• 1、 Showalter,Johnson,Hoftiezer,Turner,Werbel,Leopold,Shillis,Jackson,Elslager. "Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias". . p. 121 - 131. Retrieved 2007/10/02.