Journal of medicinal chemistry

N-(5, 5-diacetoxypent-1-yl) doxorubicin: a new intensely potent doxorubicin analog

A Cherif, D Farquhar

Index: Cherif, Abdallah; Farquhar, David Journal of Medicinal Chemistry, 1992 , vol. 35, # 17 p. 3208 - 3214

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Citation Number: 46

Abstract

N-(5, 5-Diacetoxypent-l-yl) doxorubicin (DAPDOX)(3), a new, water-soluble analogue of doxorubicin, has been synthesized by coupling doxorubicin with 5-oxopentane-1, l-diacetate in the presence of NaBH&N. This analogue was designed to be converted to the corresponding aldehyde, N-(5-oxopent-l-yl) doxorubicin, in the presence of carboxylate hydrolases, enzymes that are ubiquitous in tissue. DAPDOX had a half-life of several days ...