Collect. Czech. Chem. Commun. 1980, 45, 3583-3592
https://doi.org/10.1135/cccc19803583

Some ω-(2-amino-6-hydroxy-4-oxo-3,4-dihydro-5-pyrimidinyl) alkanoic acids, their derivatives and analogues

Miroslav Semonský, Antonín Černý, Jiří Křepelka, Rudolf Kotva, Bohumil Kakáč, Jiří Holubek and Jaroslav Vachek

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3

Abstract

Condensation of 1,1,ω-alkanetricarboxylic acids triethyl esters XIV-XXI with guanidine gave ω-(2-amino-6-hydroxy-4-oxo-3,4-dihydro-5-pyrimidinyl) alkanoic acids I-IV, VI-VIII, XIII of which some were converted to derivatives (ethyl ester V, N-acyl derivatives XI and XII). Similarly, triester XVII gave by condensation with urea or thiourea the analogous 5-substituted derivatives of barbituric acid X, and thiobarbituric acid IX, respectively. The structures of selected compounds of this group (IV, V, IX-XI and XIII) were determined by spectral methods. Of interest, from the pharmacological point of view, has proved compound IV, which exhibited a significant antineoplastic effect on some experimental tumours in mice and rats, and enhanced the action of some current cytostatics.