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Synthesis and In vitro Activity of N- sulfonylamidine-derived Pyrimidine Analogues

Two novel series of N-sulfonylamidino pyrimidine derivatives were synthesized via Cu- catalyzed three-component reaction of propargylated nucleobases with different benzenesulfonyl azides and amines. In this way 4-acetamido, 4-methyl and 4- carboxybenzenesulfonyl amidine products 15–26 in the uracil series and 4- acetamidobenzenesulfonyl amidine derivatives 27–29 in the cytosine series were prepared in 34−69 % yields. Attempts to prepare N- sulfonylamidino cytosine derivatives in reaction with 4- methylbenzenesulfonyl azide were unsuccessful. The cytosine derivatives 32 and 33 were prepared from the N-sulfonylamidino uracil derivatives via the C4 triazole intermediates. The prepared N- sulfonylamidino pyrimidine derivatives 1–28 were tested for the antiproliferative activity on a panel of seven tumor cell lines of different histological origin (HeLa, Caco-2, NCI-H358, Raji, HuT78, K562, Jurkat) and on normal MDCK I cells. Most of the synthesized compounds showed antiproliferative activity on the tested cell lines.

pyrimidines, N-sulfonylamidines, multi-component synthesis, copper(I), in vitro.

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