Five-stage synthetic scheme for obtaining of N-substituted 1-benzyltheobromine-8- hioglicolacetamides was described. The intermediate compound 1-benzyl-8- romotheobromine was synthesized using aliquat 336 as phase transfer catalyst in very good yield. Five amide derivatives of 1-benzyltheobromine-8-thioglicolyc acid were obtained in yields of 61 to 81%. The structures of the studied compounds were established by FTIR, 1H NMR spectral data. In order to estimate the drug-likeness of compounds 7a-e, a theoretical calculation of some molecular descriptors was made using two approaches: the Lipinski`s Rule of Five limitations and the OSIRIS Property Explorer evaluation score. The comparison of the calculated results indicate that only one compound violates the Lipinski`s Rule of Five parameters - 7c, which makes it unsuitable for further structural optimizations. On the other hand compound 7e shows the highest drug like properties with Fragment Based Druglikeness score of 2.58 and total Drug score of 0.43 which are better than the same scores of parent compound theobromine.
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