Synthesis and antitumor activity of 3’-deamino-3’-hydroxydoxorubicin: A facile procedure for the preparation of doxorubicin analogs

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Abstract

Two successful routes have been developed for preparation of 3’-deamino-3’-hydroxy-doxorubicin (11), based on protection of the 14-hydroxyl group of the aglycon by using tert-butylchlorodimethylsilane. The key intermediate, 14-o-tert-butyldimethylsilyl-7-O-(3,4-di-O-acety]-2,6-dideoxy-a-L-/>’.Y0-hexopyranosyl)adriamycinone (9), was successively deacetylated and desilylated in high yield to give the desired product 11. This route constitutes a general method of access to glycon-modified doxorubicin analogs. Compound 11 showed high antitumor activity in vivo in the murine P388 lymphocytic leukemia assay. © 1984, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.

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Horton, D., Priebe, W., & Varela, O. (1984). Synthesis and antitumor activity of 3’-deamino-3’-hydroxydoxorubicin: A facile procedure for the preparation of doxorubicin analogs. Journal of Antibiotics, 37(8), 853–858. https://doi.org/10.7164/antibiotics.37.853

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