Synthesis and chemical properties of a series of doxorubicin enaminomalonyl-β-alanine derivatives

A series of doxorubicin enaminomalonyl-β-alanine derivatives 1a-e has been synthesized as potential drug-linker domains of an antibody drug conjugate. The release of doxorubicin from these enamide derivatives under acidic and neutral conditions has been evaluated. Two activated esters, 6a and 6c, su...

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Bibliographic Details
Published inTetrahedron letters Vol. 36; no. 9; pp. 1413 - 1416
Main Authors Seitz, David E., Ezcurra, John E., Guttman-Carlisle, Deborah L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.02.1995
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTITUMOR-ACTIVITY
ADRIAMYCIN
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Summary:A series of doxorubicin enaminomalonyl-β-alanine derivatives 1a-e has been synthesized as potential drug-linker domains of an antibody drug conjugate. The release of doxorubicin from these enamide derivatives under acidic and neutral conditions has been evaluated. Two activated esters, 6a and 6c, suitable for coupling to a monoclonal antibody have been prepared. Hydrolytic release of doxorubicin from a series of doxorubicin enaminomalonyl-β-alanine derivatives. [Display omitted]
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00019-9