68594-06-9

Basic information

• Product Name: N-(Trifluoroacetyl)-1-desMethyl Daunorubicin
• Synonyms: N-(Trifluoroacetyl)-1-desMethyl Daunorubicin;(8S,10S)-8-acetyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-10-[[2,3,6-trideoxy-3-[(trifluoroacetyl)aMino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione;(8S-cis)-8-Acetyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-10-[[2,3,6-trideoxy-3-[(trifluoroacetyl)aMino]-α-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione
• CAS NO: 68594-06-9
• Molecular Formula: C₂₈H₂₆F₃NO₁₁
• Molecular Weight: 609.5013496
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68594-06-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Acetone
• CAS DataBase Reference: N-(Trifluoroacetyl)-1-desMethyl Daunorubicin(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Trifluoroacetyl)-1-desMethyl Daunorubicin(68594-06-9)
• EPA Substance Registry System: N-(Trifluoroacetyl)-1-desMethyl Daunorubicin(68594-06-9)

Safety Data

• Hazardous Substances Data: 68594-06-9(Hazardous Substances Data)

Usage

Chemical Properties

Red Solid

Uses

Daunorubicinc (D194500) derivative.

Upstream product

• 52794-97-5 carminomycin I hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 26388-52-3 3'-N-trifluoroacetyldaunorubicin 
• 23541-50-6 daunomycin hydrochloride 

Downstream Products

• 50935-04-1 carminomycin 
• 57852-57-0 idarubicin hydrochloride 

Relevant articles and documents

METHOD OF PRODUCING 4-DEMETHOXYDAUNORUBICIN

The present invention relates to a method for the synthesis of 4-demethoxydaunorubicin (idarubicin) having the chemical structure of formula (I), which involves the demethylation of 3′-Prot-daunorubicin in the presence of a soft Lewis acid. The method of the present invention does not comprise cleavage of the glycosidic linkage at carbon C7, thus resulting in a faster synthesis cycle and an improved yield of the final product.

14-Esters and 13-Hydrazones of Anthracycline Antibiotics of the Daunorubicin Series: Synthesis and Cytostatic Activity toward Tumor Cells Sensitive or Resistant to Doxorubicin

Doxorubicin and 14-hydroxycarminomycin 14-O-hemiadipates and 14-O-hemipimelates (synthesized from 14-bromo derivatives of daunorubicin, carminomycin monosodium adipate, and pimelate) were converted to the corresponding N-trifluoroacetylated compounds. 13-(4-methylpiperazine-1-yl)imino derivatives of the anthracycline antibiotics were also obtained.The cytostatic activity of the compounds synthesized was studied using a panel of human and animal tumor cell lines sensitive or resistant to doxorubicin.N-Trifluoroacetylation of the antibiotics resulted in a decrease in the cytostatic activity.The activity of the water-soluble 13-(4-methylpiperazine-1-yl)imino derivatives is close to that of the corresponding parent antibiotics. - Keywords: anthracycline antibiotics; multidrug resistance