Estrella Saniger, J. Campos, A. Entrena
Sep 29, 2003
Citations
0
Influential Citations
35
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction between o -(hydroxymethyl)phenoxyacetaldehyde dimethyl acetals, or 3-methoxy-2,3-dihydro-5 H -1,4-benzodioxepins with 5-fluorouracil (5-FU), has been studied. The intramolecular cyclization may be explained through a neighboring group attack to give a 2-(5-fluorouracil-1-yl)oxyranium ion that can be attacked by the silylated benzylic hydroxy group to yield the benzannelated seven-membered O , N -acetals. The formation of a macrocyclic trans -bis(5-FU O , N -acetal) is also reported. Such a compound arrested the human MCF-7 breast cancer cells at the G o /G 1 phase of the cell cycle. On the contrary, the acyclic nitro O , N -acetal seems to work as a 5-FU prodrug, because it arrested cancer cells at the S phase as the well-known prodrug Ftorafur does.