26388-52-3

Usage

Chemical Properties

Red Solid

Uses

Protected Daunorubicin.

InChI:InChI=1/C29H28F3NO11/c1-10-22(35)14(33-27(40)29(30,31)32)7-17(43-10)44-16-9-28(41,11(2)34)8-13-19(16)26(39)21-20(24(13)37)23(36)12-5-4-6-15(42-3)18(12)25(21)38/h4-6,10,14,16-17,22,35,37,39,41H,7-9H2,1-3H3,(H,33,40)/t10-,14-,16-,17-,22+,28-/m0/s1

Upstream product

• 26295-55-6 14-iodo-N-(trifluoroacetyl)daunorubicin 
• 23541-50-6 daunomycin hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 20830-81-3 DNR 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 219921-59-2 3'-N,4'-O-di-trifluoroacetyldaunomycin 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 130767-70-3 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin 
• 83945-39-5 N-Trifluoracetyldaunorubicin 
• 57918-22-6 4'-epi-N-(trifluoroacetyl)daunorubicin 
• 83945-38-4 N-[(2S,3R,4R,6R)-6-((1S,3S)-3-Acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide 
• 130767-72-5 Benzoic acid (2R,3R,4S,6R)-6-[(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-4-amino-2-methyl-tetrahydro-pyran-3-yloxy]-4-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester 
• 130767-71-4 C₄₃H₄₄F₃NO₁₅ 
• 68594-06-9 4-demethyl-3'-trifluoroacetamido-daunorubicine 
• 57852-57-0 idarubicin hydrochloride 
• 57918-24-8 4’-epidaunorubicin 

Relevant academic research and scientific papers

Preparation method for idarubicin hydrochloride

The invention belongs to the field of drug synthesis, and discloses a preparation method for idarubicin hydrochloride. The idarubicin hydrochloride is prepared by adopting a metal nickel catalyst / anorganic phosphine ligand / a silane reducing agent to remove a methoxy group located at a 4-position of an anthracycline compound in one step. According to the invention, the method has the advantages that the steps are short and the synthesis costs are reduced, can reduce generation of an impurity A and an impurity B, and improves the quality of the final product idarubicin hydrochloride.

Epirubicin hydrochloride intermediate compound IV

The invention provides a novel intermediate and a new route for synthesizing epirubicin hydrochloride by using the intermediate. The route is simple, cheap and efficient, and meanwhile, the problems that the intermediate generated by an existing epirubicin hydrochloride synthesis route is instable in water and easy to decompose and the whole route is low in yield are solved. In order to better achieve energy conservation and emission reduction, a cheap and available reagent is utilized by the route; and meanwhile, removable selective protection means are adopted, so that the generated impurities are few, the purity is high and the yield is high.

Epirubicin hydrochloride than star-intermediate compound (by machine translation)

The present invention provides novel intermediates and utilizing the intermediate synthesis than the star of epirubicin hydrochloride new routes. The route is simple, low-cost, high-efficiency, at the same time avoiding the existing epirubicin hydrochloride than star-synthetic route to produce the intermediate with water not stable, easily decomposed, the overall line rate is on the low side, in order to better energy-saving and emission reduction, the routes using low cost and easily obtained reagent; at the same time adopts the removable selective protection means, produce little impurity, high purity, high yield. (by machine translation)

A hydrochloric acid the table is supple than star process for the preparation of intermediates

The invention relates to a preparation method for an intermediate 4'-epidaunorubicin hydrochloride of epirubicin hydrochloride. The preparation method comprises the steps of trifluoroacetyl protection, oxidation, reduction, hydrolyzation, etc. The method effectively inhibit generation of (methylthio)methyl ether, increases selectivity for sodium borohydride during the reduction process and is mild in reaction conditions. The total yield of the reaction is over 40% (based on epidaunorubicin hydrochloride) and the purity reaches 99.5%.

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 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.

EPIMERIZATION OF 4'-C BOND AND MODIFICATION OF 14-CH3-(CO)-FRAGMENT IN ANTHRACYCLIN ANTIBIOTICS

A method of synthesizing Rl, R2-substituted-4' (ax. or eq.)-OH anthracyclines and their corresponding salts of Formula (1) from daunorubicin or N-Trifluoroacetyl-4- Rl - derivatives of daunorubicin, wherein Rl is defined as H, OH, and 4'-HO is defined as ax[ial]. The method includes producing N-Trifluoroacetyl daunorubicin and treating the N- Trifluoroacetyldaunorubicin or N-Trifluoroacetyl-4-R1 -derivatives of daunorubicin, wherein R1 is defined as H, OH, with dimethylsulfoxide activated by different acylating agents. The attained intermediate product is then treated with a strong base (ex. tertiary amines) resulting in the 4 -keto-N-Trifluoroacetyl-4-R1 daunorubicin wherein Ri is defined as H, OH, OMe. The 4-keto-N-Trifluoroacetyl-4-R1 -daunorubicin is reacted with a reducing agent, a derivative of a borohydride of an alkaline metal MHBL3 ,to produce N- Trifluoroacetyl-4'-epi-4-R1 -daunorubicin. The N-Trifluoroacetyl-4'-epi-4-R1 -daunorubicin undergoes hydrolysis in a basic solution to produce a derivate of an anthoacyclin which is halogenized [by complex halogenidesjto form a 14-Hal-derivative. This result is then hydrolyzed by well-known methods in the presence of a formate of an alkaline metal to form the desired final compound.

Syntheses and biological activity of bisdaunorubicins

To study the length and flexibility of the linkers between two monomers of bisdaunorubicins for their activity against cancer cells, seven bisdaunorubicins were rationally designed and synthesized through click chemistry. Their cytotoxicity was tested in

Syntheses and biological activities of 3′-azido disaccharide analogues of daunorubicin against drug-resistant leukemia

Anthracyclines, such as daunorubicin (DNR) and doxorubicin (Dox), are widely used for cancer therapy but are limited by drug resistance and cardiotoxicity. To overcome drug resistance, we synthesized a novel class of disaccharide analogues of DNR against

MULTIDRUG RESISTANT ANTICANCER ANTHRACYCLINES

Daunorubicin ("DNR") compounds synthesized with uncommon sugars exhibit enhanced effectiveness in treating various drug-resistant cancers.