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

Autori
Krstulović, Luka ; Saftić, Dijana ; Ismaili, Hamit ; Bajić, Miroslav ; Glavaš-Obrovac, Ljubica ; Žinić, Biserka

Izvornik
Croatica chemica acta (0011-1643) 90 (2017), 4; 625-636

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

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

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA