Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Syntheses of Idarubicin Analogues Containing a Glucose or Galactose Moiety as a Glycone

  • Rho, Young-S. (Department of Chemistry, Chonbuk National University) ;
  • Park, Ran (Department of Chemistry, Chonbuk National University) ;
  • Kim, Seon-Young (Biochemistry of Medical School, Chonbuk National University) ;
  • Yoo, Dong-Jin (Department of Chemistry, Seonam University)
  • Published : 2010.01.20
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Abstract

The new idarubicin analogues (12 and 13) with a glucose or galactoseas as a glycone were synthesized from daunomycin (2). (+)-4-Demethoxydaunomycinone (6) obtained from reaction of 2 with $AlCl_3$ was converted to 4-trifluoromethanesulfonyl daunomycinone (7) through reaction with trifluoromethanesulfonic anhydride. The treatment of 7 with 1,1-bis-(diphenylphospino)ferrocene/$Pd(OAc)_2$ in triethylamine/formic acid/dioxane provided the idarubicinone (5b). Glycosylation of 7-hydroxy group of 5b with two kinds of tetraacetyl pyranosyl halide (8 and 9) by a modified Koenigs-Knorr procedure and then deacetylation using aqueous 0.1 N LiOH solution and amberlite cationic resin gave the objective materials. The in vitro MTT assay of the analogues (12b and 13a) in comparison with idarubicin (5a) on peripheral blood human promyelocytic-leukemia cell line and human breast cancer cell line were also described.

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