68594-06-9

Usage

Chemical Properties

Red Solid

Uses

Daunorubicinc (D194500) derivative.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

METHOD FOR PREPARING 4-DEMETHYLDAUNORUBICIN

A method of preparing the anthracyclin carminomycin using a starting material comprising daunorubicin. The method comprises reacting daunorubicin or N-protected daunorubicin with soft Lewis acids for the demethylation of the 4-methoxy group, resulting in a reaction mass. The reaction mass is treated with an aqueous solution of a strong organic acid or a mineral acid. After decomposition of the resulting carminomycin and Lewis acids reactive complex, the reaction mass is extracted using a water insoluble organic solvent. As a result, carminomycin is extracted as a base.

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

The synthesis of epsilon-rhodomycinone- and carminomycin-11-methyl ethers.

The conversion of epsilon-rhodomycinone to its 11-methyl ether via selective hydrolysis of the 4,6,7,11-tetraacetate is described. This series of reactions was used as a model for the conversion of carminomycin to its 11-methyl ether. The anti-tumor activity of the latter compound was less than that of both carminomycin and its 4-methyl ether (daunomycin).