Synthesis and Antitumor Activity of New Anthracycline Analogues

New anthracycline analogues 2-9 as potential anticancer agents have been synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2 and 6 were prepared by the nucleophilic displacement type esterification of 14-bromodaunomycin (1c) with N-benzoyl-(2R,3S)-phenylisoserine and L-pyroglutamic ac...

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Published inBulletin of the Korean Chemical Society Vol. 22; no. 9; pp. 963 - 968
Main Authors 김완중, 유동진, 강현수, 장순량, Young S. Rho, Kim, Wan Jung, Yu, Dong Jin, Gang, Hyeon Su, Jang, Sun Ryang
Format Journal Article
LanguageKorean
Published 2001
Subjects
Anthracycline deribvatives
N-Benzoyl-(2R,3S)-phenylisoserine
Daunomycin
Doxorubicin
L-Pyroglutamic acid
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Summary:New anthracycline analogues 2-9 as potential anticancer agents have been synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2 and 6 were prepared by the nucleophilic displacement type esterification of 14-bromodaunomycin (1c) with N-benzoyl-(2R,3S)-phenylisoserine and L-pyroglutamic acid in triethyl-amine, respectively. Compounds 3, 7 and 4, 8 were prepared by the reaction of either daunomycin (1a) or doxorubicin (1b) with one equivalent of the corresponding acids in the presence of EDCI/PP. Compounds 5, 9 were obtained from 1b by reaction with 2.2 equivalents of the corresponding acids in the same manner. The cytotoxic activities of the analogues in comparison with adrimycin on cultured SNU-16 and MCF7 cell were described.
Bibliography:KISTI1.1003/JNL.JAKO200113464479123
ISSN:0253-2964
1229-5949