2. Academic Validation
  3. 7-(Aminoethyl) ether and thioether of daunomycinone

7-(Aminoethyl) ether and thioether of daunomycinone

  • J Med Chem. 1979 Aug;22(8):922-6. doi: 10.1021/jm00194a007.
E M Acton,  G L Tong,  C W Mosher,  T H Smith,  D W Henry
PMID: 490537 DOI: 10.1021/jm00194a007
Abstract

One-step treatment of daunomycinone with excess 2-aminoethanethiol and 2-aminoethanol in trifluoroacetic acid afforded at C-7 the thioether (77% yield) and ether (30% after recycling), respectively. Stereoselectivity for the natural 7S over the 7R configuration was greater for the ether (97:3) than for the thioether (2.5:1). Esterification of daunomycin at C-7 with beta-alanine was accomplished through the mixed anhydride of Z(OMe)-beta-alanine. Preliminary biological tests suggests that the antitumor and DNA interactive properties of the anthracyclines can be retained in such structures.

Figures