Studies of antitumor agents. 1. Resolution of racemic 1-(tetrahydro-2-furanyl)-5-fluorouracil into the R and S isomers and examination of the biological activities of the isomers

Article abstract of DOI:10.1021/jm00222a011

1-(Tetrahydro-2-furanyl)-5-fluorouracil (Thf-FU), which is named Ftorafur or FT-207 and is used clinically as an antitumor agent, was conveniently synthesized by condensation of the trimethylsilyl derivative of 5-fluorouracil with 2-acetoxytetrahydrofuran using NaI as a catalyst. This optically inactive Thf-FU was resolved into optically active (R) (+) and (S) (-) Thf-FU in high optical purity and excellent yield by formation of diastereoisomers with brucine. ¹³C NMR data were obtained on Thf-FU and related compounds and the antibacterial activities and in vivo antitumor activities of these isomers were tested. The degradations of these isomers to 5-fluorouracil by liver microsomes were also examined. No significant differences were found in any of these properties of these isomers.