Studies of antitumor agents. 1. Resolution of racemic 1-(tetrahydro-2-furanyl)-k-fluorouracil into the R and S isomers and examination of the biological activities of the isomers.
J Med Chem, 1977/12;20(12):1592-4.
Yasumoto M, Moriyama A, Unemi N, Hashimoto S, Suzue T
PMID: 338900
Impact factor: 8.039
Abstract
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.
MeSH terms
Animals; Bacteria; Fluorouracil; In Vitro Techniques; Male; Mice; Microsomes, Liver; Neoplasms, Experimental; Rats; Stereoisomerism; Structure-Activity Relationship; Tegafur
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