181943-72-6

Basic information

• Product Name: (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-(3-tert-butoxycarbonylamino-propoxymethyl)-1,2,3,4-tetrahydro-naphthacen-2-yl ester
• Synonyms: (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-(3-tert-butoxycarbonylamino-propoxymethyl)-1,2,3,4-tetrahydro-naphthacen-2-yl ester
• CAS NO: 181943-72-6
• Molecular Weight: 718.801
• Mol File: 181943-72-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-(3-tert-butoxycarbonylamino-propoxymethyl)-1,2,3,4-tetrahydro-naphthacen-2-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-(3-tert-butoxycarbonylamino-propoxymethyl)-1,2,3,4-tetrahydro-naphthacen-2-yl ester(181943-72-6)
• EPA Substance Registry System: (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-(3-tert-butoxycarbonylamino-propoxymethyl)-1,2,3,4-tetrahydro-naphthacen-2-yl ester(181943-72-6)

Safety Data

• Hazardous Substances Data: 181943-72-6(Hazardous Substances Data)

Upstream product

• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 163129-96-2 (1R,5S,7R)-3-Ethyl-2-oxo-6,8-dioxa-3-aza-bicyclo[3.2.1]octane-7-carboxylic acid (R)-12-acetoxy-2-acetyl-5-bromomethyl-1,2,3,4-tetrahydro-naphthacen-2-yl ester 

Relevant articles and documents

Asymmetric synthesis and DNA intercalation of (-)-6-[[(aminoalkyl)oxy]methyl]-4-demethoxy-6,7-dideoxydaunomycinones

The BF3·Et2O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptan e led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen- 2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopentyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dion e hydrochloride (-)-8, (-)-9, (-)-16, respectively, as well as (8R)-8-acetyl-6,8-dihydroxy-11-[[[2'-[(3''-aminopropyl)amino]ethyl]oxy ]-((-)-11) and -[[3'-[(3''-aminopropyl)amino]propyl]oxy]methyl]-7,8,9,10-tetrahydrona phthacene-5,12-dione hydrochloride ((-)-12). (8R)-8-Acetyl-6,8-dihydroxy-11-[[(α-L-daunosaminyl)oxy]methyl]-7,8,9, 10-tetrahydronaphthacene-5,12-dione hydrochloride ((-)-13), a mimic of idarubicin, was also prepared. Absorbance and fluorescence titration experiments showed (-)-8, (-)-9, and (-)-16 to intercalate calf thymus DNA whereas (-)-11, (-)-12, and (-)-13 did not. The best intercalator was (-)-9 (K(b) = (1.1 ± 0.1) x 105 M-1) with the [(4'-aminobutyl)oxy]-methyl chain. Inhibition of topoisomerase II-induced DNA strand religation was observed for (-)-8 at a concentration of 50 μM.