104319-02-0

Basic information

• Product Name: (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione
• Synonyms: (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione
• CAS NO: 104319-02-0
• Molecular Weight: 393.396
• Mol File: 104319-02-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: >300 °C
• Boiling Point: 721.1±60.0 °C(Predicted)
• Density: 1.49±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione(104319-02-0)
• EPA Substance Registry System: (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione(104319-02-0)

Safety Data

• Hazardous Substances Data: 104319-02-0(Hazardous Substances Data)

Usage

General Description

(R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione, also known as (R)-Epirubicin, is a synthetic anthracycline antibiotic and antineoplastic agent that is used in chemotherapy to treat various types of cancer. It works by inhibiting the replication of DNA and RNA, ultimately leading to the destruction of cancer cells. (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione is a potent cytotoxic agent, and it is particularly effective against breast, ovarian, and lung cancers, as well as non-Hodgkin's lymphomas. However, it can also cause significant side effects such as myelosuppression, gastrointestinal toxicity, and cardiotoxicity, which limits its use in certain patient populations. Despite its drawbacks, (R)-Epirubicin continues to be an important tool in the treatment of cancer and is a key component of many chemotherapy regimens.

Upstream product

• 85-44-9 phthalic anhydride 
• 86264-61-1 (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 

Downstream Products

• 86264-76-8 (R)-(-)-9-acetamido-9-<1,1-(ethylenedioxy)ethyl>-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 110267-81-7 Amrubicin 

Relevant articles and documents

Stereospecific Total Synthesis of 9-Aminoanthracyclines: (+)-9-Amino-9-deoxydaunomycin and Related Compounds

9-amino-9-deoxydaunomycin and related compounds, in which the hydroxyl group at the 9-position of daunomycin is replaced by an amino group, have been synthesized.Asymmetry was introduced into the synthetic sequence for the AB synthon by resolution of the intermediate amino ester or acetamido acid to afford (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, which was converted to the tetracyclic amido ketones by Friedel-Crafts acylation with phthalic anhydride or its 3-methoxy derivative.The resulting regioisomers 4- and 1-methoxy compounds were separed, after methylation and selective demethylation, by crystallization and preparative TLC.The required introduction of the C7-hydroxyl function proceeded stereosepcifically via a three-step reaction sequence involving formation of an oxazine compound.The silver trifluoromethane assisted glycosidation of the resulting aglycons with 2-deoxy-3,4-di-O-acetyl-D-erythro-pentopyranosyl bromide or N,O-bis(trifluoroacetyl)daunosaminyl chloride, followed by alkaline hydrolysis afforded the target glycosides.The work reported herein comprises an efficient, practical synthesis of 9-amino-9-deoxydaunomycin and its analogues with the same stereochemistry as in the naturally occurring anthracyclines.