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

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

Uses

Used in Oncology:
(R)-Epirubicin is used as a chemotherapy agent for the treatment of various types of cancer. It is particularly effective against breast, ovarian, and lung cancers, as well as non-Hodgkin's lymphomas. (R)-(-)-9-acetyl-9-acetamido-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione's mechanism of action involves the inhibition of DNA and RNA replication, which disrupts the cancer cells' ability to proliferate and survive.
Used in Drug Development:
(R)-Epirubicin serves as a key component in the development of new chemotherapy regimens and drug combinations. Its potent cytotoxic effects make it a valuable tool in the fight against cancer, and ongoing research aims to minimize its side effects and improve its efficacy in combination with other treatments.
Used in Cancer Research:
As a potent cytotoxic agent, (R)-Epirubicin is also utilized in cancer research to study the mechanisms of action and resistance in various types of cancer. Understanding these processes can lead to the development of more targeted and effective therapies.
Despite its effectiveness, (R)-Epirubicin can cause significant side effects such as myelosuppression, gastrointestinal toxicity, and cardiotoxicity. These side effects may limit its use in certain patient populations, and ongoing research is focused on finding ways to mitigate these drawbacks while maintaining the drug's therapeutic benefits.

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

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

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.

A method for synthesizing ammonia supple ratio star

The invention discloses a synthetic method for amrubicin. R-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene is used as a raw material, and is subjected to acylation and cyclization with phthalic anhydride. 1,3-propanediol and derivatives thereof are used to protect carbonyl, and the protective group is liable to remove in a hydrolysis reaction. The amrubicin is prepared by a step of subjecting (+)-9-amino-4-demethoxy-9-deoxy-daunomycinone with 2-deoxy-3,4-di-O-acetyl-beta-D-erythro-pentapyranosyl-1,1,1-trichloroiminoacetate to a nucleoside-forming reaction to obtain (+)-9-amino-4-demethoxy-9-deoxy-7-O-(2-deoxy-3,4-di-O-acteyl-beta-D-erythro-pentapyranosyl) daunomycinone, and a step of removing acetyl. The synthetic method can avoid generation of isomers during a hydrolysis process effectively. The synthetic method has simple subsequent purification steps. The nucleoside-forming reaction can decrease the production cost effectively. The synthetic method is suitable for industrial applications.