tert-butyloxycarbonyl-5-fluorouracil

tert-butyloxycarbonyl-5-fluorouracil (Boc-5-FU) is a protected derivative and potential prodrug of the antineoplastic antimetabolite 5-fluorouracil (5-FU). It consists of the 5-FU molecule where a tert-butyloxycarbonyl (Boc) group is attached, typically to the N1 position of the pyrimidine ring. This modification is often employed in chemical synthesis to protect the nitrogen atom or to increase the lipophilicity of the parent drug for improved delivery. As a prodrug, it is designed to undergo chemical or enzymatic hydrolysis to release active 5-fluorouracil. Once released, 5-FU exerts its cytotoxic effects by inhibiting thymidylate synthase and incorporating into RNA and DNA, thereby disrupting nucleic acid synthesis and inducing apoptosis in rapidly dividing cancer cells. It is primarily investigated in preclinical research as a model for stimuli-responsive drug delivery systems.

Other names

1-(tert-butoxycarbonyl)-5-fluorouracilN1-Boc-5-fluorouracilN-1-Boc-5-fluorouracilN 1-Boc-5-fluorouraciltert-butyl 5-fluoro-2,4-dioxo-3,4-dihydropyrimidine-1(2H)-carboxylate