Collect. Czech. Chem. Commun. 1987, 52, 2061-2069

Hydrophilic 1-(carboxymethyl)-5-fluorouracil amides: Preparation and cytostatic activity

Helmut Pischela, Antonín Holýb, Jiří Veselýb, Günther Wagnera and Dieter Cechc

a Sektion Biowissenschaften-Pharmazie, Karl-Marx-Universität, DDR-7010 Leipzig, G.D.R.
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
c Sektion Chemie, Humboldt-Universität, Berlin, G.D.R.


The following N-substituted amides IV were prepared by reaction of 1-(carboxymethyl)-5-fluorouracil p-nitrophenyl ester (II) with primary or secondary hydroxyalkylamines III: 2-hydroxypropyl (IVa), 3-hydroxypropyl (IVb), 2,3-dihydroxypropyl (IVc), 3-hydroxy-2-methyl-2-propyl (IVd), 1,3-dihydroxy-2-propyl (IVe), 1-deoxyglucitol-1-yl (IVg), 2-deoxyglucitol-2-yl (IVh), methyl-2,3-dihydroxypropyl (IVi), methyl-1-deoxyglucitol-1-yl (IVk), and n-butyl-2,3-dihydroxypropyl (IVl). None of these compounds had any cytostatic activity towards murine leukemia L-1210 cell growth in a tissue culture at 10-5 mol l-1.