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
Mechanistic studies of the reduction of daunomycin with sodium borohydride. Formation and reaction of borate esters
Schweitzer, Barbara Ann,Egholm, Michael,Koch, Tad H.
, p. 242 - 248 (2007/10/02)
Reduction of daunomycin with excess sodium borohydride in methanol degassed with prepurified nitrogen yielded 89% daunomycinol and 11% recovered daunomycin. Monitoring of the reaction by UV-vis spectroscopy revealed the formation of an intermediate with absorptions at 336 and 430 nm, which was assigned the borate ester structure 5 on the basis of the UV-vis absorption bands together with high-field 1H NMR, FTIR, and mass spectral data. Similar results were obtained upon reduction without nitrogen degassing. In contrast, sodium borohydride reduction under strictly anaerobic conditions, achieved with freeze-thaw degassing, predominantly yielded the products of glycosidic cleavage, 7-deoxydaunomycinol (6, 58%) along with daunomycinol (4, 17%). The sequential formation of two intermediates was observed: first, borate ester 5 and second, a longer lived intermediate with absorptions at 360 and 580 nm. The second intermediate is proposed to be 7-deoxydaunomycinol quinone methide borate ester (9) on the basis of the absorption bands, lifetime, and product structures compared with those observed upon reduction with the one-electron reducing agent, bi(3,5,5-trimethyl-2-oxomorpholin-3-yl) (TM-3 dimer). Reduction of 7-deoxydaunomycinone with excess sodium borohydride in nitrogen-degassed methanol yielded 42% 7-deoxydaunomycinol (6), 31% 5,7-dideoxydaunomycinol tautomer (1,2,3,4-tetrahydro-2,11-dihydroxy-2-(1-hydroxyethyl)-7-methoxy-5,12- naphthacenedione, 11), and 27% 7,12-dideoxydaunomycinol tautomer (1,2,3,4-tetrahydro-2,6-dihydroxy-2-(1-hydroxyethyl)-7-methoxy-5,12- naphthacenedione, 12). Again an intermediate with absorptions at 336 and 430 nm was observed, in this case, assigned to regioisomeric borate esters 13 and 14 on the basis of formation of regioisomeric dideoxydaunomycinol tautomers 11 and 12. The intermediacy of long-lived borate esters is relevant to the interpretation of studies employing sodium borohydride for the reductive activation of anthracyclines.
