Synthesis and biological activities of some uronic acids, uronates, uronamides, and urononitriles of pyrimidine nucleosides

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Abstract
The 5''-hydroxymethylene function of several uracil and cytosine nucleosides was modified to produce a variety of uronic acids, uronates, uronamides and urononitriles of 2''-deoxy-.beta.-D-erythro-pentofuranosyl- and .beta.-D-arabino-pentofuranosylpyrimidines. In addition, the 5 position in many of these nucleosides was substituted by a halogen atom. Compounds [21/35] were synthesized and examined for biological activity. The purity of the products was measured by a high-pressure liquid chromatographic method. They were then evaluated as potential growth inhibitors of murine Sarcoma 180 cells in culture, of herpes simplex virus type 1 in vitro, and of Streptococcus faecium, a folic acid or deoxythymidine dependent bacterial strain. The ability of nucleoside analogs to inhibit the phosphorylation of deoxythymidine by herpes simplex virus type 1 encoded pyrimidine deoxyribonucleoside kinase was investigated and a structure activity relationship examined.