94991-07-8Relevant academic research and scientific papers
SOME DERIVATIVES OF 5-(2-AMINO-6-HYDROXY-4-OXO-3,4-DIHYDRO-5-PYRIMIDINYL)PENTANOIC ACID
Krepelka, Jiri,Cerny, Antonin,Kotva, Rudolf,Vachek, Jaroslav,Melka, Milan
, p. 1140 - 1149 (2007/10/02)
Using the chloride method esters II-X, amides XI-XIV, and condensates with amino acid esters XV-XVII were prepared from 5-(2-amino-6-hydroxy-4-oxo-3,4-dihydro-5-pyrimidinyl)-pentanoic acid (I); the amides XIII and XIV were also prepared by aminolysis of ester II.The derivative of glycine, XVIII, was obtained on saponification of ester XV, also obtained by condensation of triethyl ester of N-(6,6-dicarboxyhexanoyl)glycine (XXIII) with guanidine hydrochloride in a medium containing sodium ethylate.Hydrazinolysis of ethyl ester XXIV gave hydrazide XIX.Disubstituted ureas XX-XXI were obtained on reaction of esters VI and XXIV with 2-chloroethyl isocyanate; saponification of the ester function in the urea derivative XX led to the free acid XXII.Reaction of acid I with an excess of diazomethane gave a mixture of compounds in which compound XXV (a product of esterification and O-methylation) and XXVI ( a product of esterification, O-methylation, and N-methylation) predominated.None of the substances prepared displayed a clear anti-tumour activity.Some of the substances tested affected the weight of experimental tumours ( XV, XVI, XX, XXV ) or protracted the survival time of experimental animals (XXVI, XX).Substance XX had the broadest spectrum of activity.
