Biological Studies of Analogs of Orotic Acid : 6—Uracil sulfonic Acid, 6-Uracilsulfonamide, and 6-Uracil Methyl Sulfone * WILLIAM L. HOLMES AND ARNOLD D. WELCH
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چکیده
Investigations of the metabolism of orotic acid have shown that this compound is utilized by cer thin bacteria (@O)and by the mammal for the syn thesis of pentosenucleic acid (1, 5). Although it has not been definitely established that orotic acid (or a metabolic derivative of it) is an obligatory inter mediate in the biosynthesis of nucleic acids, there is considerable evidence in support of this possi bility (15, 16). An approach to the elucidation of the biological significance of orotic acid is afforded by the design, synthesis, and biological investigation of potential antimetabolites of this compound. Conceivably, active compounds of this class could have chemo therapeutic utility by virtue of an interference with the utilization of orotic acid or its deriva tives, if qualitative or quantitative differences in their action on different types of cells were to be encountered. The well established antimetabolic activity of sulfonic acids, sulfonamides, and sub stituted sulfones analogous to certain naturally cc curring carboxylic acids suggested an investigation of similar analogs of orotic acid. The syntheses and chemistry of compounds of this new series have been presented elsewhere (@,3). In the present study it has been shown that the parent compound, 6-uracilsulfonic acid, is relative ly ineffective as a growth inhibitor of Lactobacil ins bulgaricus 09. On the other hand, 6-uracil sulfonamide and 6-uracil methyl sulfone inhibited the growth of this organism noncompetitively, as well as that of another orotic acid-utilizing strain, namely, Lactobacillus bulgariciss (Hanson). These compounds were found to have little if any effect on the growth of Streptococci@ss faecali@8043 or of Leuconostoc citrovorum (Pediococcus cerevi@iae)
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