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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 13
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Original Articles

SYNTHESIS OF NEW ANTHRACYCLINE DERIVATIVES CONTAINING PYRUVIC, ASPARTIC, OR N-ACETYLASPARTIC ACID MOLECULE

, , , , , & show all
Pages 1961-1975 | Received 23 Jun 2001, Published online: 16 Aug 2006
 

ABSTRACT

The new anthracycline analogues (2–10) as potential anticancer agents were synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2, 6, and 7 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a sodium pyruvate, aspartate, and N-acetylaspartic acid, respectively. Whereas compounds (3, 8) and (4, 9) were prepared by the reaction of daunomycin (1a) or doxorubicin (1b) with one equivalent of the corresponding acids in the presence of EDCI/PP, compounds (5, 10) were obtained from 1b by reaction with two equivalents of the corresponding acids in the same manner.

ACKNOWLEDGMENT

This work was supported by a grant of the Korea Health 21 R&D project (HMP-98-D-4-0026), Ministry of Health & Welfare, Republic of Korea.

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