1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione hydrochloride

Base Information

• Chemical Name: 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione hydrochloride
• CAS No.: 70476-82-3
• Molecular Formula: C22H28N4O6. 2HCl
• Molecular Weight: 517.409
• Hs Code.: 29146100
• NSC Number: 758450,301739
• ChEMBL ID: CHEMBL1200827
• Mol file: 70476-82-3.mol

Synonyms:Acetate, Mitoxantrone;CL 232325;CL-232325;CL232325;DHAQ;Hydrochloride, Mitoxantrone;Mitoxantrone;Mitoxantrone Acetate;Mitoxantrone Hydrochloride;Mitozantrone;Mitroxone;Novantron;Novantrone;NSC 279836;NSC 287836;NSC 299195;NSC 301739;NSC 301739D;NSC-279836;NSC-287836;NSC-299195;NSC-301739;NSC-301739D;NSC279836;NSC287836;NSC299195;NSC301739;NSC301739D;Onkotrone;Pralifan;Ralenova

Chemical Property of 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione hydrochloride

Chemical Property:

• Melting Point: 203-205 °C
• Boiling Point: 805.7 °C at 760 mmHg
• Flash Point: 441.1 °C
• PSA: 163.18000
• LogP: 2.39260
• Storage Temp.: 2-8°C
• Solubility.: Sparingly soluble in water, slightly soluble in methanol, practically insoluble in acetone.
• Water Solubility.: Soluble to 5 mM in water and to 75 mM in DMSO
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 480.1775624
• Heavy Atom Count: 33
• Complexity: 571

Purity/Quality:

99% ^*data from raw suppliers

Mitoxantrone dihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,T+
• Hazard Codes: T,T+
• Statements: 46-61-26/27/28
• Safety Statements: 53-36/37/39-45-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO.Cl
• Description: Mitoxantrone hydrochloride is the first of the synthetic anthracenediones related to doxorubicin to reach the marketplace. Mitoxantrone is useful in the treatment of advanced localized and metastatic mammary carcinomas. It is reported to be less cardiotoxic than doxorubicin. Mitoxantrone is an anthraquinone that intercalates in DNA and inhibits topoisomerase II (IC50 = 5.3 μM), thus inhibiting cell proliferation. It also inhibits HIV-1 integrase (IC50 = 3.8 μM). Mitoxantrone is exported from cells in an ATP- and glutathione-dependent manner by multidrug resistance protein-1. Formulations containing mitoxantrone have been used in the treatment of cancer and multiple sclerosis.
• Uses: Mitoxanthrone hydrochloride USP (Novantrone) is used to traet acute nonlymphocytic leukemia, including myelogenous promyelocytic, monocytic, and erythroid acute leukemias. Mitoxantrone dihydrochloride is an antiviral, antibacterial, antiprotozoal, immunomodulating, and antineoplastic cytostatic anthraquinone derivative. Induces DNA damage by intercalating into DNA and inhibiting Topo II (topoisomerase II). Mitoxantrone dihydrochloride induces interstrand DNA cross-links and DNA-protein cross-links in cellular systems. Mitoxantrone dihydrochloride has recently been shown to be an inhibitor of DNA methylation.
• Therapeutic Function: Antineoplastic
• Clinical Use: Mitoxantrone is used in combination with other agents during the initial treatment of acute nonlymphocytic leukemia and hormone-refractory prostate cancer. Recent studies have shown that mitoxantrone also decreases the rate of relapse and disease progression in patients with multiple sclerosis. Although too toxic for use in patients with primary progressive disease, it is available for the treatment of chronic progressive, progressive relapsing, or deteriorating relapsing-remitting multiple sclerosis.

Technology Process of 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione hydrochloride

There total 4 articles about 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione hydrochloride 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:

novantrone (65271-80-9,70945-62-9) → novantrone (70476-82-3)

Guidance literature:

With hydrogenchloride; In water; at 52 - 60 ℃; for 0.5h; pH=Ca. 2.8 - 3; Temperature; Inert atmosphere;

Reference yield:

5,8-dihydroxy-1,4-bis<<2-hydroxyethyl>amino>-9,10-anthracenedione (3179-90-6) → novantrone (70476-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / pyridine / 4 h / Ambient temperature

2: 2.) hydrochloric acid / 1.) acetonitrile-DMA, 0.8 h, reflux, 2.) ether

With pyridine; hydrogenchloride;

Reference yield:

ethanolamine (141-43-5) + 5,8-dihydroxy-1,4-bis<(2-p-toluensulfonyloxyethyl)amino>anthracene-9,10-dione (111228-29-6) → novantrone (70476-82-3)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction; 1.) acetonitrile-DMA, 0.8 h, reflux, 2.) ether;

upstream raw materials:

ethanolamine

5,8-dihydroxy-1,4-bis<(2-p-toluensulfonyloxyethyl)amino>anthracene-9,10-dione

5,8-dihydroxy-1,4-bis<<2-hydroxyethyl>amino>-9,10-anthracenedione

novantrone

Refernces

• 1、 -. "Novel 1,4-bis(substituted-amino(-5,8-dihydroxyanthraquinones and leuco bases thereof". . . Retrieved 2008/06/13.
• 2、 -. "Metal chelates of 1,4-bis(substituted-amino-5,8-dihydroxy-anthraquinones". . . Retrieved 2008/06/13.