engleski

N-Sulfonylamidine Cytosine Derivatives

Recently we reported on efficient one-pot synthesis of novel N-sulfonylamidino thymine derivatives by Cu(I) catalyzed three component reaction of 1-propargyl thymine, selected benzenesulfonyl azides and amines [1]. We show that this one-pot three component reaction appears to be favourable for the preparation of variously substituted N-sulfonylamidino thymine derivatives in moderate to good yields and opens the way for preparation of libraries of other nucleobase N-sulfonylamidino derivatives as potential biologically active molecules. Here we report on the synthesis of novel N-sulfonylamidine derivatives in cytosine series. When the Cu(I)-catalyzed three-component coupling reactions was performed with 1-propargyl cytosine 1 the yields on amidine derivatives 2 were relatively low. Hence, the approach to 2 via the N-sulfonyamidine uracil derivatives 3 was explored. The N-sulfonyamidine uracil derivatives 3 obtained in good yields by Cu(I) catalyzed three component reaction were treated with 1-(mesitylene-2-sulfonyl)-3-nitro-1, 2, 4-triazole (MSNT) in the presence of diphenylphosphate to give 4-triazolylpyrimidinone intermediates. The latter compounds in the reaction with ammonium hydroxide in dioxane gave the cytosine derivatives 2 in the much better yields. Obtained derivatives were tested for their cytostatic activity.

N-Sulfonylamidine; cytosine; click reaction;

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