16234-96-1

Basic information

• Product Name: aklavinone
• Synonyms: aklavinone;(±)-2-Ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;(1R,2R,4S)-2-Ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;Aclavinone
• CAS NO: 16234-96-1
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.3894
• Mol File: 16234-96-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 663.5°Cat760mmHg
• Flash Point: 235°C
• Appearance: /
• Density: 1.525g/cm³
• Vapor Pressure: 1.64E-18mmHg at 25°C
• Refractive Index: 1.683
• PKA: 6.50±0.70(Predicted)
• CAS DataBase Reference: aklavinone(CAS DataBase Reference)
• NIST Chemistry Reference: aklavinone(16234-96-1)
• EPA Substance Registry System: aklavinone(16234-96-1)

Safety Data

• Hazardous Substances Data: 16234-96-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H20O8/c1-3-22(29)8-13(24)15-10(17(22)21(28)30-2)7-11-16(20(15)27)19(26)14-9(18(11)25)5-4-6-12(14)23/h4-7,13,17,23-24,27,29H,3,8H2,1-2H3

Upstream product

• 78773-24-7 (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 83862-11-7 {4,5-Dihydroxy-3-[(S)-1-((1R,2R)-2-hydroxy-1-methyl-propoxy)-3-oxo-pentyl]-9,10-dioxo-9,10-dihydro-anthracen-2-yl}-acetic acid methyl ester 
• 92471-67-5 (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((1R,2R)-2-hydroxy-1-methyl-propoxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 78773-14-5 (3-Formyl-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetic acid methyl ester 
• 83862-10-6 [3-((4R,5R)-4,5-Dimethyl-[1,3]dioxolan-2-yl)-4,5-dihydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl]-acetic acid methyl ester 
• 78773-17-8 9-epi-aklavinone 7-methyl ether 
• 78773-17-8 7-epi-aklavinone 7-methyl ether 
• 78773-17-8 aklavinone 7-methyl ether 
• 16234-96-1 (+/-)-Aklavinon-I 
• 78821-97-3 (+/-)-aklavinone 
• 78773-21-4 7-(tetrahydropyranyl)-10-epi-aklavinone 
• 78773-21-4 7-(tetrahydropyranyl)aklavinone 
• 92449-49-5 (3-Formyl-4-formyloxy-5-hydroxy-9,10-dioxo-9,10-dihydro-anthracen-2-yl)-acetic acid methyl ester 
• 78773-13-4 (10-Hydroxy-6,11-dioxo-6,11-dihydro-anthra[1,2-b]furan-4-yl)-acetic acid methyl ester 

Downstream Products

• 116235-59-7 Aklaviketone 
• 57576-44-0 aclacinomycin A 
• 60504-57-6 aklavin 
• 78773-24-7 (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 78773-24-7 (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 65222-75-5 N-demethylaklavin 
• 65222-75-5 (1S,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((2R,4S,5S,6S)-5-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 21288-61-9 Epsilon-pyrromycinone 
• 77607-10-4 3',3'-didesmethyl-aclarubicin 

Related news

A convergent rgiospecific route to the aklavinone (cas 16234-96-1) ring system08/07/2019

A convergent regiospecific route to the aklavinone (II) ring system is described.detailed

A formal total synthesis of aklavinone (cas 16234-96-1) via a blocked anthraquinone tautomer08/06/2019

An advanced intermediate in the Kishi synthesis of aklavinone was prepared. Juglone was converted into enone 4. Quinone 6 was then prepared from 4 by Michael addition and elimination of PhSOH and HCN.detailed

Enantioselective synthesis of the AB ring system of aklavinone (cas 16234-96-1) via a chemoenzymatic route08/05/2019

The AB ring system 2 of aklavinone 1 was obtained using a chemoenzymatic protocol. Key steps are the stereoselective addition of lithium enolate of ethyl acetate to ketone 13 and the intramolecular Friedel-Crafts reaction to give tetralin 17.detailed

Modification of aklavinone (cas 16234-96-1) and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products07/31/2019

The rdm genes B, C and E from Streptomyces purpurascens encode enzymes that tailor aklavinone and aclacinomycins. We report that in addition to hydroxylation of aklavinone to ϵ-rhodomycinone, RdmE (aklavinone-11-hydroxylase) hydroxylated 11-deoxy-β-rhodomycinone to β-rhodomycinone both in vivo...detailed

Relevant articles and documents

Facile Regio- and Stereoselective Total Synthesis of Racemic Aklavinone

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Doxorubicin and Aclarubicin: Shuffling Anthracycline Glycans for Improved Anticancer Agents

Anthracycline anticancer drugs doxorubicin and aclarubicin have been used in the clinic for several decades to treat various cancers. Although closely related structures, their molecular mode of action diverges, which is reflected in their biological activity profile. For a better understanding of the structure-function relationship of these drugs, we synthesized ten doxorubicin/aclarubicin hybrids varying in three distinct features: Aglycon, glycan, and amine substitution pattern. We continued to evaluate their capacity to induce DNA breaks, histone eviction, and relocated topoisomerase IIα in living cells. Furthermore, we assessed their cytotoxicity in various human tumor cell lines. Our findings underscore that histone eviction alone, rather than DNA breaks, contributes strongly to the overall cytotoxicity of anthracyclines, and structures containing N,N-dimethylamine at the reducing sugar prove that are more cytotoxic than their nonmethylated counterparts. This structural information will support further development of novel anthracycline variants with improved anticancer activity.

1(4H)-Naphthalenones in Anthracyclinone Synthesis: A New Route for the Total Synthesis of (+/-)-Aklavinone

A brief route for total synthesis of (+/-)-aklavinone (1a), the aglycon of the anticancer antibiotic aclacinomycin (1b), is described.Key features of the synthesis are the development of a brief, efficient route to the 1(4H)-naphthalenone 11, which was used as a synthon for the A and B rings, and homologation of keto aldehyde 17 to the keto anthraquinone acetic ester 16 via the intermediacy of the ketene thioacetal 19.