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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 6
BKCSDE 22(6)
June 20, 2001 

Synthesis of New Anthracycline Derivatives Containing Acetylsalicylic or Palmitic Acid Moiety
Young S. Rho, Gyuil Kim, Wan-Joong Kim, Siho Park, Dong Jin Yoo, Heun Soo Kang, Soon-Ryang Chung
Daunomycin, Doxorubicin, Anthracycline, Acetylsalicyclic acid, Palmitic acid.
The potential anticancer agents new anthracycline derivatives (2-9) have been synthesized from daunomycin (1a) and doxorubicin (1b) as starting materials. Compounds 2 and 6 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a acetylsalicylic and palmitic acid in triethylamine, respectively. Compounds 3 and 7 were obtained from daunomycin (1a) by direct amidation with the corresponding acids in the presence of EDCI and PP as esterification reagents. Whereas 4 and 8 were prepared by reaction of doxorubicin (1b) with one equivalent of acetylsalicylic and palmitic acid using DCC/DMAP, respectively, 5 and 9 were obtained from 1b by acylation with two equivalents of the corresponding acids using EDCI/PP reagents.
587 - 592
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