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

Krstulović, Luka; Saftić, Dijana; Ismaili, Hamit; Bajić, Miroslav; Glavaš-Obrovac, Ljubica; Žinić, Biserka (2018) Synthesis and In vitro Activity of N-sulfonylamidine-derived Pyrimidine Analogues. Croatica Chemica Acta, 90 (4). pp. 625-636. ISSN 0011-1643

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Abstract

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.

Item Type: Article
Uncontrolled Keywords: pyrimidines; N-sulfonylamidines; multi-component synthesis; copper(I); in vitro
Subjects: NATURAL SCIENCES
NATURAL SCIENCES > Chemistry
NATURAL SCIENCES > Chemistry > Organic Chemistry
NATURAL SCIENCES > Biology
NATURAL SCIENCES > Biology > Microbiology
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Dijana Saftić
Date Deposited: 02 May 2018 12:42
Last Modified: 02 May 2018 12:42
URI: http://fulir.irb.hr/id/eprint/4017
DOI: 10.5562/cca3273

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