One-electron reduction characteristics of N(3)-substituted 5-fluorodeoxyuridines synthesized as radiation-activated prodrugs

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Abstract

We designed and synthesized N(3)-substituted 5-fluorodeoxyuridines as radiation-activated prodrugs of the antitumor agent, 5-fluorodeoxyuridine (5-FdUrd). A series of 5-FdUrd derivatives possessing a 2-oxoalkyl group at the N(3)-position released 5-FdUrd in good yield via one-electron reduction initiated by hypoxic irradiation. Cytotoxicity of the 5-FdUrd derivative possessing the 2-oxocyclopentyl group (3d) was low, but was enhanced by hypoxic irradiation resulting in 5-FdUrd release. © 2003 Elsevier Ltd. All rights reserved.

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Tanabe, K., Mimasu, Y., Eto, A., Tachi, Y., Sakakibara, S., Mori, M., … Nishimoto, S. I. (2003). One-electron reduction characteristics of N(3)-substituted 5-fluorodeoxyuridines synthesized as radiation-activated prodrugs. Bioorganic and Medicinal Chemistry, 11(21), 4551–4556. https://doi.org/10.1016/j.bmc.2003.08.001

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