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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 Including Butyric or Retinoic Acid Moiety
Young S. Rho, Wan-Joong Kim, Siho Park, Dong Jin Yoo, Heun Soo Kang, Soon-Ryang Chung
Daunomycin, Doxorubicin, Anthracycline derivatives, Butyric and retinoic acid, Acylation.
The potential anticancer agents, new anthracycline analogues (2-9) have been synthesized from the glycosides daunomycin (1a) and doxorubicin (1b). Compounds 2 and 6 were prepared by nucleophilic displacement esterification of a 14-bromodaunomycin (1c) with sodium or potassium salts of butyric and all trans retinoic acid, respectively. Compounds 3 and 7 were obtained from daunomycin (1a) by direct amidation with a butyric and all trans retinoic acid in the presence of EDCI and PP, respectively. Compounds 4 and 8 were obtained from doxorubicin (1b) by reaction with the corresponding acids in the same manner. Compounds 5 and 9 were prepared from doxorubicin (1b) by acylation with two equivalents of the corresponding acids under the same reaction conditions.
581 - 586
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