Search for new biologically active compounds based on 6-methyluracil-5-sulfochloride and alcohols
DOI:
https://doi.org/10.15587/2312-8372.2018.124272Keywords:
biologically active compounds, synthesis of alkyl sulfonates based on 6-methyluracil-5-sulfochloride and alcoholates, reactivityAbstract
The object of research is the interaction of 6-methyluracil-5-sulfochloride (MUSC) with aliphatic alcohols (C1–C10) in order to obtain new methyl ether sulfate esters not described in the literature. With the help of the PAAS program, it is shown that these esters exhibit biological activity. They exhibit antioxidant properties, and can also find use as cytostatics.
One of the most problematic places in the synthesis of methyluracyl sulfonic esters is obtaining the final compounds in the most pure form and with the greatest yield. This goal is achieved by the fact that the used alcohol is previously absolute, heating it with calcium oxide or calcined copper sulfate. In the obtained absolute alcohol, the quota part of Na or K is dissolved, and after the reaction termination, the quoted portion of MUSC is added.
In the course of the studies, the principle of sulfochlorination of methyluracil is changed. In order to increase the yield and improve the quality of the final product, the reaction of methyluracil with freshly distilled chlorosulfonic acid is carried out in an inert solvent such as dichloroethane, followed by the addition of thionyl chloride.
To improve the quality of synthesized compounds and simplify the synthesis, the methyluracil used is reacted with metallic sodium or potassium to form an alcoholate. Further, the obtained alcoholate reacts with the calculated amount of the sulfochloride, forming an almost chemically pure final product.
With the help of the program, the preliminary biological activity of synthesized compounds is determined and the possibility of using the compounds obtained as cytostatics is determined. And with the help of NMR spectroscopy and elemental analysis, the composition and structure of the obtained compounds are confirmed, the data of which are given in the form of a table.
A number of new compounds not described in the literature have been obtained. This is due to the fact that the proposed method has a number of features, in particular, the use of available raw materials, the improvement of synthesis methods.
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