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

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 inac...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1977-12, Vol.20 (12), p.1592-1594
Main Authors: Yasumoto, M, Moriyama, A, Unemi, N, Hashimoto, S, Suzue, T
Format: Article
Language:English
Subjects:
Animals
Bacteria - drug effects
Fluorouracil - analogs & derivatives
In Vitro Techniques
Male
Mice
Microsomes, Liver - metabolism
Neoplasms, Experimental - physiopathology
Rats
Stereoisomerism
Structure-Activity Relationship
Tegafur - chemical synthesis
Tegafur - isolation & purification
Tegafur - metabolism
Tegafur - pharmacology
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Summary: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.
ISSN:0022-2623