32384-98-8Relevant articles and documents
Reduction of daunomycin and 11-deoxydaunomycin with sodium dithionite in DMSO. Formation of quinone methide sulfite adducts and the first NMR characterization of an anthracycline quinone methide
Gaudiano,Frigerio,Sangsurasak,Bravo,Koch
, p. 5546 - 5553 (1992)
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14-Fluoroanthracyclines. Novel syntheses and antitumor activity
Matsumoto,Ohsaki,Yamada,Matsuda,Terashima
, p. 3793 - 3804 (1988)
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Electrophilic trapping of the tautomer of 7-deoxydaunomycinone. A possible mechanism for covalent binding of daunomycin to DNA
Kleyer,Koch
, p. 5154 - 5155 (1983)
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Design, synthesis and antitumor activities of novel 7-arylseleno-7-deoxydaunomycinone derivatives
Zhang, Shu-Jia,Jia, Zheng-Ping,Wang, Yan-Guang
, p. 3899 - 3904 (2002)
7-Arylseleno-7-deoxydaunomycinone derivatives 3a-e and 7-thiophenyl-7-deoxydaunomycinones (7 and 8) were synthesized and the antitumor activities of them were evaluated against human stomach cancer SGC-7901 and human leukaemia HL60. The cytotoxic assay sh
Asymmetric synthesis of anthracyclinones: Regio- and stereoselective synthesis of (-)-7-deoxydaunomycinone through direct asymmetric introduction of an alkynyl unit into C9 ketone
Fujioka,Yamamoto,Annoura,Miyazaki,Kita
, p. 1872 - 1876 (1990)
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A facial synthesis of 7-selenodaunomycinone derivatives
Zhang, Shu Jia,Wang, Yan Guang
, p. 520 - 521 (2007/10/03)
7-selenodaunomycinone derivatives 3a-e were synthesised by condensation of daunomycinone 2 with aryl selenols catalysed by trifluoroacetic acid in dichloromethane at room temperature. When the concentration of aryl selenol exceeds 2 to 2-3 times, 7-deoxyd
Reduction of daunomycin in dimethyl sulfoxide. Long-lived semiquinones and quinone methide and formation of an enolate at the 14-position via the quinone methide
Gaudiano, Giorgio,Frigerio, Massimo,Bravo, Pierfrancesco,Koch, Tad H.
, p. 3107 - 3113 (2007/10/02)
Anaerobic reduction of daunomycin (1, daunorubicin) in 5%/95% H2O/DMSO (DMSO = dimethyl sulfoxide) or in DMSO with sodium dithionite or bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer), respectively, yields 7-deoxydaunomycinone (7) and a mixture of the diastereomers of bi(7-deoxydaunomycinon-7-yl) (8). A precursor to both 7 and 8 is 7-deoxydaunomycinone quinone methide (4) formed from glycosidic cleavage of daunomycin hydroquinone (3). The hydroquinone 3 is estabished as a precursor to the quinone methide 4 from relative rates. In 5%/95% H2O/DMSO or DMSO, daunomycin semiquinone (2) and quinone methide (4) have much longer lifetimes than in 100% protic solvents such as H2O or methanol. The quinone methide reacts to form the side chain enolate most likely by intramolecular proton transfer from the methyl group at the 14-position to the 7-position.